Avermectin and avemectin monosaccharide derivatives substituted in the 4&#34;-or 4&#39;-position having pesticidal properties

ABSTRACT

Disclosed are compounds of the formula in which n is 0 or 1; X—Y is —CH═CH— or —CH 2 —CH 2 —; Z is —C(═O)—, —C(═S)— or —S0 2 —; R 1  is C 1 -C 12 alkyl, C 3 -C 8 cycloalkyl or C 2 -C 12 alkenyl; and R 2  is R 3 -Z-, R 3 —O-Z-, R 4  or -Z-N(R 6 )(R 7 ); Q is O or —N—R 5 ; R 3  and R 4  are for example H, C 1 C 12 alkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 3 -C 12 zcycloalkyl, C 5 -C 12 cycloalkenyl, aryl or heterocyclyl; R 5  is for example H, C 1 -C 8 alkyl, hydroxy-C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl or benzyl; R 6  and R 7  are for example, H, unsubstituted or mono- to pentasubstituted C 1 -C 12 alkyl, unsubstituted or mono- to pentasubstituted C 2 -C 12 alkenyl or, if appropriate, an E/Z isomer, E/Z isomer mixture and/or tautomer thereof, in each case in free form or in salt form, are useful as pesticides.

The invention provides (1) a compound of the formula (I)

in which

n is 0 or 1;

X—Y is —CH═CH— or —CH₂—CH₂—;

R₁ is C₁-C₁₂alkyl, C₃-C₈cycloalkyl or C₂-C₁₂alkenyl; and

R₂ is R₃-Z-, R₃—O-Z-, R₄ or -Z-N(R₆)(R₇);

Z is —C(═O)—, —C(═S)— or —SO₂—;

Q is O or —N—R₅;

R₃ and R₄ are H, C₁-C₁₂alkyl, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl,C₃-C₁₂cycloalkyl, C₅-C₁₂cycloalkenyl, aryl or heterocyclyl, wherein thealkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl and heterocyclylradicals may be—depending on the substitutionpossibilities—unsubstituted or mono- to pentasubstituted; either

R₅ is H, C₁-C₈alkyl, hydroxy-C₁-C₈alkyl, C₃-C₈cycloalkyl, C₂-C₈alkenyl,C₂-C₈alkynyl, phenyl, benzyl, —C(═O)—R₉, or —CH₂—C(═O)—R₉; or,

when Q is NR₅ and R₂ is R₄,

R₄ and R₅ together are a three- to seven-membered alkylene- oralkenylene-bridge, which is unsubstituted or mono- to tri-substituted;or a three- to seven-membered alkylene- or alkenylene-bridge, which areunsubstituted or mono- to tri-substituted, and in which one or two ofthe methylene groups of the bridge are replaced by O, NR₈, S, S(═O) orSO₂;

R₆ and R₇ are, independently from each other, H, unsubstituted or mono-to pentasubstituted C₁-C₁₂alkyl, unsubstituted or mono- topentasubstituted C₂-C₁₂alkenyl, unsubstituted or mono- topentasubstituted C₂-C₁₂alkynyl, unsubstituted or mono- topentasubstituted C₃-C₁₂-cycloalkyl, unsubstituted or mono- topentasubstituted C₅-C₁₂cycloalkenyl, unsubstituted or mono- topentasubstituted aryl, or unsubstituted or mono- to pentasubstitutedheterocyclyl; or

R₆ and R₇ together are a three- to seven-membered alkylene- oralkenylene-bridge, which are unsubstituted or mono- to tri-substituted;or a three- to seven-membered alkylene- or alkenylene-bridge, which areunsubstituted or mono- to tri-substituted, and in which one or two ofthe methylene groups of the bridge are replaced by O, NR₈, S, S(═O) orSO₂;

R₈ is H, C₁-C₈alkyl, hydroxy-C₃-C₈alkyl, C₃-C₈cycloalkyl, C₂-C₈alkenyl,C₂-C₈alkynyl, phenyl, benzyl, —C(═O)R₉ or —CH₂—C(═O)—R₉;

in which the substituents of the alkyl, alkenyl, alkynyl, alkylene,alkenylene, cycloalkyl, cycloalkenyl, aryl and heterocyclyl radicalsmentioned under R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are selected from thegroup consisting of OH, ═O, SH, ═S, —N₃, halogen, halo-C₁-C₂alkyl, CN,SCN, NO₂, trialkylsilyl, C₁-C₁₂alkyl, C₁-C₁₂-haloalkyl, C₂-C₈alkenyl,C₂-C₆haloalkenyl, C₂-C₈alkynyl, C₃-C₈cycloalkyl that is unsubstituted orsubstituted by one to three methyl groups, norbornylenyl,C₃-C₈halocycloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂alkoxy-C₁-C₁₂alkoxy,C₁-C₁₂haloalkoxy, C₃-C₈cycloalkoxy, C₁-C₁₂alkylthio,C₃-C₈cycloalkylthio, C₁-C₁₂-haloalkylthio, C₁-C₁₂alkylsulfinyl,C₃-C₈cycloalkylsulfinyl, C₁-C₁₂haloalkylsulfinyl,C₃-C₈halocycloalkylsulfinyl, C₁-C₁₂alkylsulfonyl,C₃-C₈cycloalkylsulfonyl, C₁-C₁₂haloalkylsulfonyl,C₃-C₈halocycloalkylsulfonyl, —N(R₁₂)₂ wherein the two R₁₂ areindependent of each other, —C(═O)R₉, —O—C(═O)R₁₀, —NHC(═O)R₉,—S—C(═S)R₁₀, —P(═O)(OC₁-C₆alkyl)₂, —S(═O)₂R₁₃, —NH—S(═O)₂R₁₃,—OC(═O)—C₁-C₆alkyl-S(═O)₂R₁₃, aryl, benzyl, heterocyclyl, aryloxy,benzyloxy, heterocyclyloxy, arylthio, benzylthio and heterocyclylthio;wherein the aryl, heterocyclyl, aryloxy, benzyloxy, heterocyclyloxy,arylthio, benzylthio or heterocyclylthio radicals are unsubstituted or,depending on the possibilities of substitution on the ring, mono- topentasubstituted by substituents selected from the group consisting ofOH, halogen, ON, NO₂, C₁-C₁₂alkyl, C₃-C₈cycloalkyl, C₁-C₁₂haloalkyl,C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio,C₁-C₆alkoxy-C₁-C₆alkyl, dimethylamino-C₁-C₆alkoxy, C₂-C₈alkenyl,C₂-C₈alkynyl, phenyl, phenoxy, phenyl-C₁-C₆alkyl, methylenedioxy,—C(═O)R₉, —O—C(═O)—R₁₀, —NH—C(═O)R₁₀, —N(R₁₂)₂ wherein the two R₁₂ areindependent of each other, C₁-C₆alkylsulfinyl, C₃-C₈cycloalkylsulfinyl,C₁-C₆haloalkylsulfinyl, C₃-C₈halocycloalkylsulfinyl, C₁-C₆alkylsulfonyl,C₃-C₈cycloalkylsulfonyl, C₁-C₆haloalkylsulfonyl andC₃-C₈halocycloalkyl-sulfonyl;

R₉ is H, OH, SH, —N(R₁₂)₂ wherein the two R₁₂ are independent of eachother, C₁-C₂₄alkyl, C₂-C₁₂alkenyl, C₁-C₈hydroxyalkyl, C₁-C₁₂haloalkyl,C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₆alkoxy-C₁-C₆alkyl,C₁-C₆alkoxy-C₁-C₆alkoxy, C₁-C₆alkoxy-C₁-C₆alkoxy-C₁-C₆alkyl,C₁-C₁₂alkylthio, C₂-C₈alkenyloxy, C₃-C₈alkynyloxy,—NH—C₁-C₆alkyl-C(═O)—R₁₁, —N(C₁-C₆alkyl)-C₁-C₆alkyl-C(═O)—R₁₁,—O—C₁-C₂alkyl-C(═O)R₁₁, —C₁-C₆alkyl-S(═O)₂R₁₃, aryl, benzyl,heterocyclyl, aryloxy, benzyloxy, heterocyclyloxy; or aryl, benzyl,heterocyclyl, aryl-oxy, benzyloxy or heterocyclyloxy, which areunsubstituted or mono- to trisubstituted in the ring independently ofone another by halogen, nitro, C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆haloalkylor C₁-C₆haloalkoxy;

R₁₀ is H, C₁-C₂₄alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂hydroxyalkyl,C₂-C₈alkenyl, C₂-C₈alkynyl, C₁-C₆alkoxy-C₁-C₆alkyl, —N(R₁₂)₂ wherein thetwo R₁₂ are independent of each other, —C₁-C₆alkyl-C(═O)R₁₂,—C₁-C₆alkyl-S(═O)₂R₁₃, aryl, benzyl, heterocyclyl; or aryl, benzyl orheterocyclyl which, depending on the possibilities of substitution onthe ring, are mono- to trisubstituted by substituents selected from thegroup consisting of OH, halogen, CN, NO₂, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl,C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio andC₁-C₁₂halo-alkylthio;

R₁₁ is H, OH, C₁-C₂₄alkyl that is optionally subsituted with OH, or—S(═O)₂—C₁-C₆alkyl, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl, C₁-C₁₂alkoxy,C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkoxy, C₂-C₈alkenyloxy, aryl,aryloxy, benzyloxy, heterocyclyl, heterocyclyloxy or —N(R₁₂)₂, whereinthe two R₁₂ are independent of each other;

R₁₂H, C₁-C₆alkyl, which is optionally substituted with one to fivesubstituents selected from the group consisting of OH, ═O, halogen,C₁-C₆alkoxy, hydroxy and cyano; C₁-C₈-cycloalkyl, aryl, benzyl,heteroaryl; or aryl, benzyl or heteroaryl, which, depending on thepossibilities of substitution on the ring, are mono- to trisubstitutedby substituents selected from the group consisting of OH, halogen, CN,NO₂, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy,C₁-C₁₂alkylthio and C₁-C₁₂haloalkylthio; or the two R₁₂ together are athree- to seven-membered alkylene- or alkenylene-bridge, which isunsubstituted or mono- to tri-substituted; or a three- to seven-memberedalkylene- or alkenylene-bridge, which is unsubstituted or mono- totri-substituted, and in which one of the methylene groups of the bridgeis replaced by O, NR₈, S, S(═O) or SO₂;

R₁₃ is H, C₁-C₆alkyl that is optionally substituted with one to fivesubstituents selected from the group consisting of halogen, OH, ═O,C₁-C₆alkoxy, hydroxy and cyano; aryl, benzyl, heteroaryl; or aryl,benzyl or heteroaryl, which, depending on the possibilities ofsubstitution on the ring, are mono- to trisubstituted by substituentsselected from the group consisting of OH, ═O, halogen, CN, NO₂,C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy,C₁-C₁₂alkylthio and C₁-C₁₂haloalkylthio;

or, if appropriate, an E/Z isomer, E/Z isomer mixture and/or tautomerthereof, in each case in free form or in salt form;

a process for preparing these compounds, their isomers and tautomers andthe use of these compounds, their isomers and tautomers; pesticidalcompositions whose active compound is selected from these compounds andtheir tautomers; intermediates for the preparation of the said compoundsof the formula (I), methods for the preparation of the compounds of theformula (I), and a method for controlling pests using thesecompositions.

The literature proposes certain macrolide compounds for controllingpests. However, the biological properties of these known compounds arenot entirely satisfactory, and, as a consequence, there is still a needfor providing further compounds having pesticidal properties, inparticular for the control of insects and representatives of the orderAcarina. According to the invention, this object is achieved byproviding the present compounds of the formula (I).

The compounds claimed according to the invention are derivatives ofAvermectin. Avermectins are known to the person skilled in the art. Theyare a group of structurally closely related pesticidally activecompounds which are obtained by fermenting a strain of the microorganismStreptomyces avermitilis. Derivatives of Avermectins can be obtained byconventional chemical syntheses.

The Avermectins which can be obtained from Streptomyces avermitilis arereferred to as A1a, A1b, A2a, A2b, B1a, B1b, B2a and B2b. The compoundsreferred to as “A” and “B” have a methoxy radical and an OH group,respectively, in the 5-position. The “a” series and the “b” series arecompounds in which the substituent R₁ (in position 25) is a sec-butylradical and an isopropyl radical, respectively. The number 1 in the nameof the compounds means that atoms 22 and 23 are linked by double bonds;the number 2 means that they are linked by a single bond and that the Catom 23 carries an OH group. The above nomenclature is adhered to in thedescription of the present invention to denote the specific structuretype in the not naturally occurring Avermectin derivatives according tothe invention which corresponds to the naturally occurring Avermectin.What is for instance claimed according to the invention are derivativesof compounds of the B1 series, in particular mixtures of derivatives ofAvermectin B1, especially B1a and B1b, along with derivatives having asingle bond between carbon atoms 22 and 23, and derivatives having othersubstituents in the 25-position, as well as the correspondingmonosaccharides.

Some of the compounds of the formula (I) can be present as tautomers.Accordingly, hereinabove and hereinbelow, the compounds of the formula(I) are, if appropriate, also to be understood as including thecorresponding tautomers, even if the latter are not specificallymentioned in each case.

The compounds of formula (I) and, where applicable, their tautomers canform salts, for example acid addition salts. These acid addition saltsare formed, for example, with strong inorganic acids, such as mineralacids, for example sulfuric acid, a phosphoric acid or a hydrohalicacid, with strong organic carboxylic acids, such as unsustituted orsubstituted, for example halo-substituted, C₁-C₄alkanecarboxylic acids,for example acetic acid, unsaturated or saturated dicarboxylic acids,for example oxalic acid, malonic acid, maleic acid, fumaric acid orphthalic acid, hydroxycarboxylic acids, for example ascorbic acid,lactic acid, malic acid, tartaric acid or citric acid, or benzoic acid,or with organic sulfonic acids, such as unsubstituted or substituted,for example halo-substituted, C₁-C₄alkane- or aryl-sulfonic acids, forexample methane- or p-toluene-sulfonic acid. Compounds of formula (I)that have at least one acidic group can furthermore form salts withbases. Suitable salts with bases are, for example, metal salts, such asalkali metal salts or alkaline earth metal salts, for example sodium,potassium or magnesium salts, or salts with ammonia or with an organicamine, such as morpholine, piperidine, pyrrolidine, a mono-, di- ortri-lower alkylamine, for example ethylamine, diethylamine,triethylamine or dimethylpropylamine, or a mono-, di- ortrihydroxy-lower alkylamine, for example mono-, di- or tri-ethanolamine.Corresponding internal salts may also be formed where appropriate. Thefree form is preferred. Among the salts of the compounds of formula (I),the agrochemically advantageous salts are preferred. Hereinbefore andhereinafter, any reference to the free compounds of formula (I) or theirsalts is to be understood as including, where appropriate, also thecorresponding salts or the free compounds of formula (I), respectively.The same applies to tautomers of compounds of formula (I) and saltsthereof.

Unless defined otherwise, the general terms used hereinabove andhereinbelow have the meanings given below.

Unless defined otherwise, carbon-containing groups and compounds eachcontain from 1 up to and including 6, preferably from 1 up to andincluding 4, especially 1 or 2, carbon atoms.

Halogen—as a group per se and also as a structural element of othergroups and compounds, such as haloalkyl, haloalkoxy and haloalkylthio—isfluorine, chlorine, bromine or iodine, in particular fluorine, chlorineor bromine, especially fluorine or chlorine.

Alkyl—as a group per se and also as a structural element of other groupsand compounds, such as haloalkyl, alkoxy and alkylthio—is, in each casetaking into account the number of carbon atoms contained in each case inthe group or compound in question, either straight-chain, i.e. methyl,ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, or branched, forexample isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentylor isohexyl.

Cycloalkyl—as a group per se and also as a structural element of othergroups and compounds, such as, for example, of halocycloalkyl,cycloalkoxy and cycloalkylthio—is, in each case taking into account thenumber of carbon atoms contained in each case in the group or compoundin question, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cycloheptyl or cyclooctyl.

Alkynyl—as a group per se and also as a structural element of othergroups and compounds—is, in each case taking into account the number ofcarbon atoms and conjugated or isolated double bonds contained in thegroup or compound in question, either straight-chain, for exampleethynyl, propargyl, 2-butynyl, 3-pentynyl, 1-hexynyl, 1-heptynyl,3-hexen-1-ynyl or 1,5-heptadien-3-ynyl, or branched, for example3-methylbut-1-ynyl, 4-ethylpent-1-ynyl, 4-methylhex-2-ynyl or2-methylhept-3-ynyl. Preference is given to groups —CH₂-C₂-C₁₁alkynyl,in particular —CH₂—C₂-C₅alkynyl, especially —CH₂—C₂-C₃alkynyl.

Alkynyl—as a group per se and also as a structural element of othergroups and compounds—is, in each case taking into account the number ofcarbon atoms and conjugated or isolated double bonds contained in thegroup or compound in question, either straight-chain, for exampleethynyl, propargyl, 2-butynyl, 3-pentynyl, 1-hexynyl, 1-heptynyl,3-hexen-1-ynyl or 1,5-heptadien-3-ynyl, or branched, for example3-methylbut-1-ynyl, 4-ethylpent-1-ynyl, 4-methylhex-2-ynyl or2-methylhept-3-ynyl. Preference is given to the group—CH₂—C₂-C₁₁alkynyl, in particular —CH₂—C₂-C₅alkynyl, especially—CH₂—C₂-C₃alkynyl.

Alkylene and alkenylene are straight-chain or branched bridge members;they are in particular —(CH₂)₃—, —(CH₂)₄—, —(CH₂)₅—, —CH₂(CH₃)CH₂—CH₂—,—CH₂C(CH₃)₂—CH₂—, —CH₂—CH═CH—, —CH₂—CH═CH—CH₂ or —CH₂—CH═CH—CH₂—CH₂—.

Halogen-substituted carbon-containing groups and compounds, such as, forexample, halogen-substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyor alkylthio, can be partially halogenated or perhalogenated, where inthe case of polyhalogenation the halogen substituents can be identicalor different. Examples of haloalkyl—as a group per se and also as astructural element of other groups and compounds, such as haloalkoxy orhaloalkylthio—are methyl which is mono- to trisubstituted by fluorine,chlorine and/or bromine, such as CHF₂ or CF₃; ethyl which is mono- topentasubstituted by fluorine, chlorine and/or bromine, such as CH₂CF₃,CF₂CF₃, CF₂CCl₃, CF₂CHCl₂, CF₂CHF₂, CF₂CFCl₂, CF₂CHBr₂, CF₂CHClF,CF₂CHBrF or CClFCHClF; propyl or isopropyl which is mono- toheptasubstituted by fluorine, chlorine and/or bromine, such asCH₂CHBrCH₂Br, CF₂CHFCF₃, CH₂CF₂CF₃, CF(CF₃)₂ or CH(CF₃)₂; butyl or oneof its isomers, mono- to nonasubstituted by fluorine, chlorine and/orbromine, such as CF(CF₃)CHFCF₃ or CH₂(CF₂)₂CF₃; pentyl or one of itsisomers, mono- to undecasubstituted by fluorine, chlorine and/orbromine, such as CF(CF₃)(CHF₂)CF₃ or CH₂(CF₂)₃CF₃; and hexyl or one ofits isomers, mono- to tridecasubstituted by fluorine, chlorine and/orbromine, such as (CH₂)₄CHBrCH₂Br, CF₂(CHF)₄CF₃, CH₂(CF₂)₄CF₃ orC(CF₃)₂(CHF)₂CF₃.

Aryl is in particular phenyl, naphthyl, anthracenyl, phenanthrenyl,perylenyl or fluorenyl, preferably phenyl.

Heterocyclyl is understood as being a three- to seven-memberedmonocyclic ring, which may be saturated or unsaturated, and thatcontains from one to three hetero atoms selected from the groupconsisting of N, O and S, especially N and S; or a bicyclic ring-systemhaving from 8 to 14 ring atoms, which may be saturated or unsaturated,and that may contain either in only one ring or in both ringsindependently of one another, one or two hetero atoms selected from N, Oand S.

Heterocyclyl is in particular piperidinyl, piperazinyl, oxiranyl,morpholinyl, thiomorpholinyl, pyridyl, N-oxidopyridinio, pyrimidyl,pyrazinyl, s-triazinyl, 1,2,4-triazinyl, thienyl, furanyl,dihydrofuranyl, tetrahydrofuranyl, pyranyl, tetrahydropyranyl, pyrrolyl,pyrrolinyl, pyrrolidinyl, pyrazolyl, imidazolyl, imidazolinyl,thiazolyl, isothiazolyl, triazolyl, oxazolyl, thiadiazolyl, thiazolinyl,thiazolidinyl, oxadiazolyl, phthalimidoyl, benzothienyl, quinolinyl,quinoxalinyl, benzofuranyl, benzimidazolyl, benzpyrrolyl, benzthiazolyl,indolinyl, isoindolinyl, cumarinyl, indazolyl, benzothiophenyl,benzofuranyl, pteridinyl or purinyl, which are preferably attached via aC atom; thienyl, benzofuranyl, benzothiazolyl, tetrahydropyranyl orindolyl is preferred; in particular pyridyl or thiazolyl. The saidheterocyclyl radicals may preferrably be unsubstituted or—depending onthe substitution possibilities on the ring system—substituted by 1 to 3substituents selected from the group consisting of halogen, ═O, —OH, ═S,SH, nitro, C₁-C₆alkyl, C₁-C₆hydroxyalkyl, C₁-C₆alkoxy, C₁-C₆haloalkyl,C₁-C₆haloalkoxy, phenyl, benzyl, —C(═O)—R₁₀ and —CH₂—C(═O)—R₁₀, whereinR₁₀ is as defined for formula (I) above.

In the context of the present invention, preference is given to

(2) compounds according to group (1) of the formula (I) in which R₁ isisopropyl or sec-butyl, preferably to those in which a mixture of theisopropyl and the sec-butyl derivative is present;

(3) compounds according to group (1) of the formula (I) in which R₁ iscyclohexyl;

(4) compounds according to group (1) of the formula (I) in which R₁ is1-methyl-butyl;

(5) compounds according to one of groups (1) to (4) of the formula (I)in which n is 1;

(6) compounds according to one of groups (1) to (4) of the formula (I)in which n is 0;

(7) compounds according to one of groups (1) to (6) of the formula (I)in which X—Y is —CH═CH—;

(8) compounds according to one of groups (1) to (6) of the formula (I)in which X—Y is —CH₂CH₂—;

(9) compounds according to one of groups (1) to (8) of the formula (I),in which Q is 0;

(10) compounds according to one of groups (1) to (8) of the formula (I),in which Q is —N—R₅;

(11) compounds according to one of groups (1) to (10) of the formula (I)in which R₂ is R₃—O-Z-;

(12) compounds according to one of groups (1) to (10) of the formula (I)in which R₂ is R₃-Z-;

(13) compounds according to one of groups (1) to (10) of the formula (I)in which R₂ is R₄;

(14) compounds according to one of groups (1) to (13) and of the formula(I), in which Z is —C(═O)—;

(15) compounds according to one of groups (1) to (13) of the formula(I), in which Z is —C(═S)—;

(16) compounds according to one of groups (1) to (13) of the formula(I), in which Z is —SO₂—;

(17) compounds according to anyone of groups (1) to (8) and (10) to (16)of the formula (I), in which Q is NR₅ and R₅ is H;

(18) compounds according to anyone of groups (1) to (8) and (10) to (16)of the formula (I), in which Q is NR₅ and R₅ is C₁-C₈alkyl;

(19) compounds according to anyone of groups (1) to (8) and (10) to (16)of the formula (I), in which Q is NR₅ and R₅ is hydroxy-C₁-C₈alkyl;

(20) compounds according to anyone of groups (1) to (8) and (10) to (16)of the formula (I), in which Q is NR₅ and R₅ is C₃-C₈cycloalkyl;

(21) compounds according to anyone of groups (1) to (8) and (10) to (16)of the formula (I), in which Q is NR₅ and R₅ is C₂-C₈alkenyl;

(22) compounds according to anyone of groups (1) to (8) and (10) to (16)of the formula (I), in which Q is NR₅ and R₅ is C₂-C₈alkynyl;

(23) compounds according to anyone of groups (1) to (8) and (10) to (16)of the formula (I), in which Q is NR₅ and R₅ is phenyl;

(24) compounds according to anyone of groups (1) to (8) and (10) to (16)of the formula (I), in which Q is NR₅ and R₅ is benzyl;

(25) compounds according to anyone of groups (1) to (8) and (10) to (16)of the formula (I), in which Q is NR₅ and R₅ is —C(═O)—R₉;

(26) compounds according to anyone of groups (1) to (8) and (10) to (16)of the formula (I), in which Q is NR₅ and R₅ is —CH₂—C(═O)—R₉;

(27) compounds according to anyone of groups (1) to (12) of the formula(I), in which R₃ is unsubstituted or mono- to pentasubstitutedC₂-C₁₂alkenyl;

(28) compounds according to anyone of groups (1) to (12) of the formula(I), in which R₃ is unsubstituted or mono- to pentasubstitutedC₂-C₁₂alkynyl;

(29) compounds according to anyone of groups (1) to (12) of the formula(I), in which R₃ is unsubstituted or mono- to pentasubstitutedC₃-C₁₂-cycloalkyl;

(30) compounds according to anyone of groups (1) to (12) of the formula(I), in which R₃ is unsubstituted or mono- to pentasubstitutedC₅-C₁₂cycloalkenyl;

(31) compounds according to anyone of groups (1) to (12) of the formula(I), in which R₃ is unsubstituted or mono- to pentasubstituted aryl;

(32) compounds according to anyone of groups (1) to (12) of the formula(I), in which R₃ is unsubstituted or mono- to pentasubstitutedheterocyclyl;

(33) compounds according to anyone of groups (1) to (10) and (14) to(26) of the formula (I), in which R₂ is -Z-N(R₆)(R₇);

(34) compounds according to anyone of groups (1) to (10), (14) to (26)and (33) of the formula (I), in which R₆ and R₇ are independenty of eachother H or C₁-C₁₂alkyl;

(35) compounds according to group (33) of the formula (I), in which R₇is H;

(36) compounds according to group (33) of the formula (I), in which R₇is unsubstituted or mono- to pentasubstituted C₁-C₁₂alkyl;

(37) compounds according to of group (33) of the formula (I), in whichR₇ is unsubstituted or mono- to pentasubstituted C₂-C₁₂alkenyl;

(38) compounds according to group (33) of the formula (I), in which R₇is unsubstituted or mono- to pentasubstituted C₂-C₁₂alkynyl;

(39) compounds according to of groups (33) of the formula (I), in whichR₇ is unsubstituted or mono- to pentasubstituted C₃-C₁₂-cycloalkyl;

(40) compounds according to of group (33) of the formula (I), in whichR₇ is unsubstituted or mono- to pentasubstituted C₅-C₁₂-cycloalkenyl;

(41) compounds according to of group (33) of the formula (I), in whichR₇ is unsubstituted or mono- to pentasubstituted aryl;

(42) compounds according to of group (33) of the formula (I), in whichR₇ is unsubstituted or mono- to pentasubstituted heterocyclyl;

(43) compounds according to group (33) of the formula (I), in which R₆and R₇ together are a three membered alkylene- or alkenylene-bridge,which is unsubstituted or mono- to tri-substituted;

(44) compounds according to group (33) of the formula (I), in which R₆and R₇ together are a four membered alkylene- or alkenylene-bridge,which is unsubstituted or mono- to tri-substituted;

(45) compounds according to group (33) of the formula (I), in which R₆and R₇ together are a five membered alkylene- or alkenylene-bridge,which is unsubstituted or mono- to tri-substituted;

(46) compounds according to to group (33) of the formula (I), in whichR₆ and R₇ together are a six membered alkylene- or alkenylene-bridge,which is unsubstituted or mono- to tri-substituted;

(47) compounds according to to group (33) of the formula (I), in whichR₆ and R₇ together are a seven-membered alkylene- or alkenylene-bridge,which is unsubstituted or mono- to tri-substituted;

(48) compounds according to to group (33) of the formula (I), in whichR₆ and R₇ together are a three- to seven-membered alkylene- oralkenylene-bridge, which is unsubstituted or mono- to tri-substituted,and in which one of the methylene groups of the bridge is replaced by O;

(49) compounds according to one of to group (33) of the formula (I), inwhich and R₆ and R₇ together are a three- to seven-membered alkylene- oralkenylene-bridge, which is unsubstituted or mono- to tri-substituted,and in which one of the methylene groups of the bridge is replaced byNR₈;

(50) compounds according to to group (33) of the formula (I), in whichR₆ and R₇ together are a three- to seven-membered alkylene- oralkenylene-bridge, which is unsubstituted or mono- to tri-substituted,and in which one of the methylene groups of the bridge is replaced by S;

(51) compounds according to to group (33) of the formula (I), in whichR₆ and R₇ together are a three- to seven-membered alkylene- oralkenylene-bridge, which is unsubstituted or mono- to tri-substituted,and in which one of the methylene groups of the bridge is replaced byS(═O);

(52) compounds according to to group (33) of the formula (I), in whichR₆ and R₇ together are a three- to seven-membered alkylene- oralkenylene-bridge, which is unsubstituted or mono- to tri-substituted,and in which one of the methylene groups of the bridge is replaced bySO₂;

(53) compounds according to group (1) to (10) and (13) of the formula(I), in which Q is NR₅, R₂ is R₄ and R₄ and R₅ together are a threemembered alkylene- or alkenylene-bridge, which is unsubstituted or mono-to tri-substituted;

(54) compounds according to group (1) to (10) and (13) of the formula(I), in which which Q is NR₅, R₂ is R₄ and R₄ and R₅ together are a fourmembered alkylene- or alkenylene-bridge, which is unsubstituted or mono-to tri-substituted;

(55) compounds according to one of groups (1) to (10) and (13) of theformula (I), in which Q is NR₅, R₂ is R₄ and R₄ and R₅ together are afive membered alkylene- or alkenylene-bridge, which is unsubstituted ormono- to tri-substituted;

(56) compounds according to one of groups (1) to (10) and (13) of theformula (I), in which Q is NR₅, R₂ is R₄ and R₄ and R₅ together are asix membered alkylene- or alkenylene-bridge, which is unsubstituted ormono- to tri-substituted;

(57) compounds according to one of groups (1) to (10) and (13) of theformula (I), in which Q is NR₅, R₂ is R₄ and R₄ and R₅ together are aseven-membered alkylene- or alkenylene-bridge, which is unsubstituted ormono- to tri-substituted;

(58) compounds according to one of groups (1) to (10) and (13) of theformula (I), in which Q is NR₅, R₂ is R₄ and R₄ and R₅ together are athree- to seven-membered alkylene- or alkenylene-bridge, which isunsubstituted or mono- to tri-substituted, and in which one of themethylene groups of the bridge is replaced by 0;

(59) compounds according to one of groups (1) to (10) and (13) of theformula (I), in which Q is NR₅, R₂ is R₄ and R₄ and R₅ together are athree- to seven-membered alkylene- or alkenylene-bridge, which isunsubstituted or mono- to tri-substituted, and in which one of themethylene groups of the bridge is replaced by NR₈;

(60) compounds according to one of groups (1) to (10) and (13) of theformula (I), in which Q is NR₅, R₂ is R₄ and R₄ and R₅ together are athree- to seven-membered alkylene- or alkenylene-bridge, which isunsubstituted or mono- to tri-substituted, and in which one of themethylene groups of the bridge is replaced by S;

(61) compounds according to one of groups (1) to (10) and (13) of theformula (I), in which Q is NR₅, R₂ is R₄ and R₄ and R₅ together are athree- to seven-membered alkylene- or alkenylene-bridge, which isunsubstituted or mono- to tri-substituted, and in which one of themethylene groups of the bridge is replaced by S(═O);

(62) compounds according to one of groups (1) to (10) and (13) of theformula (I), in which Q is NR₅, R₂ is R₄ and R₄ and R₅ together are athree- to seven-membered alkylene- or alkenylene-bridge, which isunsubstituted or mono- to tri-substituted, and in which one of themethylene groups of the bridge is replaced by SO₂;

(63) compounds according to anyone of groups (1) to (10), (49) or (59)of the formula (I), in which R₈ is H;

(64) compounds according to anyone of groups (1) to (10), (49) or (59)of the formula (I), in which R₈ is C₁-C₈alkyl;

(65) compounds according to anyone of groups (1) to (10), (49) or (59)of the formula (I), in which R₈ is hydroxy-C₁-C₈alkyl;

(66) compounds according to anyone of groups (1) to (10), (49) or (59)of the formula (I), in which R₈ is C₃-C₈cycloalkyl;

(67) compounds according to anyone of groups (1) to (10), (49) or (59)of the formula (I), in which R₈ is C₂-C₈alkenyl;

(68) compounds according to anyone of groups (1) to (10), (49) or (59)of the formula (I), in which R₈ is C₂-C₈alkynyl;

(69) compounds according to anyone of groups (1) to (10), (49) or (59)of the formula (I), in which R₈ is phenyl;

(70) compounds according to anyone of groups (1) to (10), (49) or (59)of the formula (I), in which R₈ is benzyl;

(71) compounds according to anyone of groups (1) to (10), (49) or (59)of the formula (I), in which R₈ is —C(═O)—R₉;

(72) compounds according to anyone of groups (1) to (10), (49) or (59)of the formula (I), in which R₅ is —CH₂—C(═O)—R₉;

Special preference is given within the scope of the invention to thecompounds of formula (I) listed in Tables A1 to A8 and in Tables 1 to180 and, where applicable, their tautomers, their mixtures of tautomers,their E/Z isomers and mixtures of E/Z isomers.

The invention also provides a process for preparing the compounds of theformula (I) and, if appropriate, tautomers thereof, wherein

(A) for the preparation of a compound of the formula (I) as definedunder (1) a compound of the formula

which is known and which can be prepared by methods known per se, and inwhich n, X—Y and R₁ have the same meanings as given above under (1) forformula (I), and G is a protecting group, for example a trialkylsilylgroup or an ester group, is reacted with a compound of the formulaR₂-Q-NH₂, which is known and which can be prepared by methods known perse, and in which R₂ and Q have the same meaning as given above under (1)for formula (I), and subsequently cleaving the protecting group bymethods, which are known per se; or

(B) for the preparation of a compound of the formula (I) as definedunder (1) a compound of the formula

which is known and which can be prepared by methods known per se, and inwhich n, X—Y and R₁ have the same meanings as given above under (1) forformula (I), is prepared by cleaving the protecting group G of thecompound of the formula (II) as defined above, and then reacting thecompound of the formula (III) with a compound of the formula R₂-Q-NH₂,which is known and which can be prepared by methods known per se, and inwhich R₂ and Q have the same meaning as given above under (1) forformula (I), in the same manner as in process variant (A).

The comments made above in connection with tautomers of compounds offormula (I) apply analogously to the starting materials mentionedhereinabove and hereinbelow in respect of their tautomers. Thepreferences of the subsitutents are the same as for the compounds of theformula (I).

In the processes of the present invention it is preferable to use thosestarting materials and intermediates which result in the compounds offormula (I) that are especially preferred.

The invention relates to all those embodiments of the process accordingto which a compound obtainable as starting material or intermediate atany stage of the process is used as starting material and all or some ofthe remaining steps are carried out, or in which a starting material isused in the form of a derivative and/or a salt and/or its diastereomers,or, especially, is formed under the reaction conditions. For instancecompounds of formula (I) bearing a functional group in its free orprotected form can be used as starting materials for the preparation offurther compounds of formula (I). For such manipulations methods knownto the person skilled in the art can be applied.

For example a compound of formula (I) wherein R₂ is —CH₂CH₂C(═O)CH₃ canbe converted to a compound of formula (I) wherein R₂ is —CH₂CH₂OH.Further standard reactions can deliver compounds of formula (I) whereinR₂ is —CH₂CH₂OCH₂O-Alkyl and —CH₂CH₂N₃. A compound of formula (I)wherein R₂ is —CH₂CH₂N₃ can be converted to a compound of formula (I)wherein R₂ is —CH₂CH₂NH₂. Treatment of such a compound of formula (I)with Hal-COR₉ gives compounds of formula (I) wherein R₂ is—CH₂CH₂NHC(═O)R₉.

The reactions described hereinabove and hereinbelow are carried out in amanner known per se, for example in the absence or, customarily, in thepresence of a suitable solvent or diluent or of a mixture thereof, thereactions being carried out, as required, with cooling, at roomtemperature or with heating, for example in a temperature range ofapproximately from −80° C. to the boiling temperature of the reactionmedium, preferably from approximately 0° C. to approximately +150° C.,and, if necessary, in a closed vessel, under pressure, under an inertgas atmosphere and/or under anhydrous conditions. Especiallyadvantageous reaction conditions can be found in the Examples.

The reaction time is not critical; a reaction time of from about 0.1 toabout 24 hours, especially from about 0.5 to about 10 hours, ispreferred.

The product is isolated by customary methods, for example by means offiltration, crystallisation, distillation or chromatography, or anysuitable combination of such methods.

The starting materials mentioned hereinabove and hereinbelow that areused for the preparation of the compounds of formula (I) and, whereapplicable, their tautomers are known or can be prepared by methodsknown per se, e.g. as indicated below.

Process Variant (A):

Examples of solvents and diluents include: aromatic, aliphatic andalicyclic hydrocarbons and halogenated hydrocarbons, such as benzene,toluene, xylene, mesitylene, tetraline, chlorobenzene, dichlorobenzene,bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane,trichloromethane, tetrachloromethane, dichloroethane, trichloroethene ortetrachloroethene; ethers, such as diethyl ether, dipropyl ether,diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethyleneglycol monomethyl ether, ethylene glycol monoethyl ether, ethyleneglycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran ordioxane; alcohols, such as methanol, ethanol, propanol, isopropanol,butanol, ethylene glycol or glycerol; carboxylic acids, such as aceticacid, pivalic acid or formic acid; ketones, such as acetone, methylethyl ketone or methyl isobutyl ketone; carboxylic acid esters, such asmethyl acetate, ethyl acetate, or esters of benzoic acid; amides, suchas N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide,N-methyl-pyrrolidone or hexamethylphosphoric acid triamide; nitriles,such as acetonitrile or propionitrile; and sulfoxides, such as dimethylsulfoxide; and also water; or mixtures of the mentioned solvents;especially suitable are esters, ethers, alcohols, carboxylic acids, ormixtures thereof, more especially ethyl acetate, isopropyl acetate,tetrahydrofuran, acetic acid, ethanol, iso-propanol or methanol.

The reactions are advantageously carried out in a temperature range offrom about room temperature to the boiling point of the solvent used;preference being given to reaction at ambient temperature.

The reactions are advantageously carried out in the presence of a base.Such bases are known to a person skilled in the art, they include, forexample, organic bases, for example amines, such as pyridin ortrietylamine; or inorganic bases, such as, for example, hydroxides orcarbonates, for example sodium hydroxide, sodium bicarbonate orpotassium carbonate.

In another embodiment of Variant (A), the reactions are advantageouslycarried out in the absence of a base.

The reactions can be advantageously carried out in the presence of awater binding agent, which is known, such as, for example hygroscopicsalts, for example magnesium sulfate or sodium sulfate; or molecularsieves. Further examples of water binding agents are known to a personskilled in the art.

In another embodiment of Variant (A), the reactions are advantageouslycarried out in the absence of a water binding agent.

In a preferred embodiment of Variant (A) the reaction is carried out inmethanol in the presence of acetic acid and pyridine at ambienttemperature; the removal of the protecting group is subsequently carriedout in tetrahydrofuran in the presence of HF and pyridine at ambienttemperature.

Especially preferred conditions for this Process variant are describedin Examples A2.1 and A6.1.

Process Variant (B):

Examples of solvents and diluents include those listed above underProcess variant (A); especially suitable are esters, ethers, alcohols,carboxylic acids, or mixtures thereof, more especially ethyl acetate,isopropyl acetate, tetrahydrofuran, acetic acid, ethanol, iso-propanolor methanol.

The reactions are advantageously carried out in a temperature range offrom about room temperature to the boiling point of the solvent used;preference being given to reaction at ambient temperature.

The reactions are advantageously carried out in the presence of a base.Such bases are known to a person skilled in the art, they include, forexample, organic bases, for example amines, such as pyridin ortrietylamine; or inorganic bases, such as, for example, hydroxides orcarbonates, for example sodium hydroxide, sodium bicarbonate orpotassium carbonate.

In another embodiment of Variant (B), the reactions are advantageouslycarried out in the absence of a base.

The reactions can be advantageously carried out in the presence of awater binding agent, which is known, such as, for example hygroscopicsalts, for example magnesium sulfate or sodium sulfate; or molecularsieves. Further examples of water binding agents are known to a personskilled in the art.

In another embodiment of Variant (B), the reactions are advantageouslycarried out in the absence of a water binding agent.

In a preferred embodiment of Variant (B) the reaction is carried out inmethanol in the presence of acetic acid and pyridine at ambienttemperature.

Especially preferred conditions for this Process variant are describedin Examples A1.1, A3.1, A4.1, A5.1, A7.1 and A8.1.

The compounds of formula (I) may be in the form of one of the possibleisomers or in the form of a mixture thereof, in the form of pure isomersor in the form of an isomeric mixture, i.e. in the form of adiastereomeric mixture; the invention relates both to the pure isomersand to the diastereomeric mixtures and is to be interpreted accordinglyhereinabove and hereinbelow, even if stereochemical details are notmentioned specifically in every case.

The diastereomeric mixtures can be resolved into the pure isomers byknown methods, for example by recrystallisation from a solvent, bychromatography, for example high pressure liquid chromatography (HPLC)on acetylcellulose, with the aid of suitable micro-organisms, bycleavage with specific, immobilised enzymes, or via the formation ofinclusion compounds, for example using crown ethers, only one isomerbeing complexed.

Apart from by separation of corresponding mixtures of isomers, purediastereoisomers can be obtained according to the invention also bygenerally known methods of stereoselective synthesis, for example bycarrying out the process according to the invention using startingmaterials having correspondingly suitable stereochemistry.

In each case it is advantageous to isolate or synthesise thebiologically more active isomer, where the individual components havedifferent biological activity.

The compounds of formula (I) may also be obtained in the form of theirhydrates and/or may include other solvents, for example solvents whichmay have been used for the crystallisation of compounds in solid form.

The invention relates especially to the preparation processes describedin Examples A1.1 to A8.1.

In the area of pest control, the compounds of formula (I) according tothe invention are active ingredients exhibiting valuable preventiveand/or curative activity with a very advantageous biocidal spectrum anda very broad spectrum, even at low rates of concentration, while beingwell tolerated by warm-blooded animals, fish and plants. They are,surprisingly, equally suitable for controlling both plant pests andecto- and endo-parasites in humans and more especially in productivelivestock, domestic animals and pets. They are effective against all orindividual development stages of normally sensitive animal pests, butalso of resistant animal pests, such as insects and representatives ofthe order Acarina, nematodes, cestodes and trematodes, while at the sametime protecting useful organisms. The insecticidal or acaricidalactivity of the active ingredients according to the invention maymanifest itself directly, i.e. in the mortality of the pests, whichoccurs immediately or only after some time, for example during moulting,or indirectly, for example in reduced oviposition and/or hatching rate.Good activity corresponds to a mortality of at least 50 to 60%.

Successful control within the scope of the subject of the invention ispossible, in particular, of pests from the orders Lepidoptera,Coleoptera, Orthoptera, Isoptera, Psocoptera, Anoplura, Mallophaga,Thysanoptera, Heteroptera, Homoptera, Hymenoptera, Diptera,Siphonaptera, Thysanura and Acarina, mainly Acarina, Diptera,Thysanoptera, Lepidoptera and Coleoptera. Very especially good controlis possible of the following pests:

Abagrotis spp., Abraxas spp., Acantholeucania spp., Acanthoplusia spp.,Acarus spp., Acarus siro, Aceria spp., Aceria sheldoni, Acleris spp.,Acoloithus spp., Acompsia spp., Acossus spp., Acria spp., Acrobasisspp., Acrocercops spp., Acrolepia spp., Acrolepiopsis spp., Acronictaspp., Acropolitis spp., Actebia spp., Aculus spp., Aculusschlechtendali, Adoxophyes spp., Adoxophyes reticulana, Aedes spp.,Aegeria spp., Aethes spp., Agapeta spp., Agonopterix spp., Agriopisspp., Agriotes spp., Agriphila spp., Agrochola spp., Agroperina spp.,Alabama spp., Alabama argillaceae, Agrotis spp., Albuna spp., Alcathoespp., Alcis spp., Aleimma spp., Aletia spp., Aleurothrixus spp.,Aleurothrixus floccosus, Aleyrodes spp., Aleyrodes brassicae, Allophyesspp., Alsophila spp., Amata spp., Amathes spp., Amblyomma spp.,Amblyptilia spp., Ammoconia spp., Amorbia spp., Amphion spp., Amphipoeaspp., Amphipyra spp., Amyelois spp., Anacamptodes spp., Anagrapha spp.,Anarsia spp., Anatrychyntis spp., Anavitrinella spp., Ancylis spp.,Andropolia spp., Anhimella spp., Antheraea spp., Antherigona spp.,Antherigona soccata, Anthonomus spp., Anthonomus grandis, Anticarsiaspp., Anticarsia gemmatalis, Aonidiella spp., Apamea spp., Aphania spp.,Aphelia spp., Aphididae, Aphis spp., Apotomis spp., Aproaerema spp.,Archippus spp., Archips spp., Acromyrmex, Arctia spp., Argas spp.,Argolamprotes spp., Argyresthia spp., Argyrogramma spp., Argyroplocespp., Argyrotaenia spp., Arotrophora spp., Ascotis spp., Aspidiotusspp., Aspilapteryx spp., Asthenoptycha spp., Aterpia spp., Athetis spp.,Atomaria spp., Atomaria linearis, Atta spp., Atypha spp., Autographaspp., Axylia spp., Bactra spp., Barbara spp., Batrachedra spp.,Battaristis spp., Bembecia spp., Bemisia spp., Bemisia tabaci, Bibiospp., Bibio hortulanis, Bisigna spp., Blastesthia spp., Blatta spp.,Blatella spp., Blepharosis spp., Bleptina spp., Boarmia spp., Bombyxspp., Bomolocha spp., Boophilus spp., Brachmia spp., Bradina spp.,Brevipalpus spp., Brithys spp., Bryobia spp., Bryobia praetiosa,Bryotropha spp., Bupalus spp., Busseola spp., Busseola fusca, Caberaspp., Cacoecimorpha spp., Cadra spp., Cadra cautella, Caenurgina spp.,Calipitrimerus spp., Callierges spp., Callophpora spp., Callophporaerythrocephala, Calophasia spp., Caloptilia spp., Calybites spp.,Capnoptycha spp., Capua spp., Caradrina spp., Caripeta spp., Carmentaspp., Carposina spp., Carposina nipponensis, Catamacta spp., Catelaphrisspp., Catoptria spp., Caustoloma spp., Celaena spp., Celypha spp.,Cenopis spp., Cephus spp., Ceramica spp., Cerapteryx spp., Ceratitisspp, Ceratophyllus spp., Ceroplaster spp., Chaetocnema spp., Chaetocnematibialis, Chamaesphecia spp., Charanvca spp., Cheimophila spp.,Chersotis spp., Chiasmia spp., Chilo spp., Chionodes spp., Chorioptesspp., Choristoneura spp., Chrysaspidia spp., Chrysodeixis spp.,Chrysomya spp., Chrysomphalus spp., Chrysomphalus dictyospermi,Chrysomphalus aonidium, Chrysoteuchia spp., Cilix spp., Cimex spp.,Clysia spp., Clysia ambiguella, Clepsis spp., Cnaemidophorus spp.,Cnaphalocrocis spp., Cnephasia spp., Coccus spp., Coccus hesperidum,Cochylis spp., Coleophora spp., Colotois spp., Commophila spp., Conistraspp., Conopomorpha spp., Corcyra spp., Cornutiplusia spp., Cosmia spp.,Cosmopolites spp., Cosmopterix spp., Cossus spp., Costaeonvexa spp.,Crambus spp., Creatonotos spp., Crocidolomia spp., Crocidolomiabinotalis, Croesia spp., Crymodes spp., Cryptaspasma spp., Cryptoblabesspp., Cryptocala spp., Cryptophlebia spp., Cryptophlebia leucotreta,Cryptoptila spp., Ctenopseustis spp., Ctenocephalides spp., Cuculliaspp., Curculio spp., Culex spp., Cuterebra spp., Cydia spp., Cydiapomonella, Cymbalophora spp., Dactylethra spp., Dacus spp., Dadica spp.,Damalinea spp., Dasychira spp., Decadarchis spp., Decodes spp.,Deilephila spp., Deltodes spp., Dendrolimus spp., Depressaria spp.,Dermestes spp., Dermanyssus spp., Dermanyssus gallinae, Diabrotica spp.,Diachrysia spp., Diaphania spp., Diarsia spp., Diasemia spp., Diatraeaspp., Diceratura spp., Dichomeris spp., Dichrocrocis spp., Dichroramphaspp., Dicycla spp., Dioryctria spp., Diparopsis spp., Diparopsiscastanea, Dipleurina spp., Diprion spp., Diprionidae, Discestra spp.,Distantiella spp., Distantiella theobroma, Ditula spp., Diurnea spp.,Doratopteryx spp., Drepana spp., Drosphila spp., Drosphila melanogaster,Dysauxes spp., Dysdercus spp., Dysstroma spp., Eana spp., Earias spp.,Ecclitica spp., Ecdytolopha spp., Ecpyrrhorrhoe spp., Ectomyelois spp.,Eetropis spp., Egira spp., Elasmopalpus spp., Emmelia spp., mpoascaspp., Empyreuma spp., Enargia spp., Enarmonia spp., Endopiza spp.,Endothenia spp., Endotricha spp., Eoreuma spp., Eotetranychus spp.,Eotetranychus carpini, Epagoge spp., Epelis spp., Ephestia spp.,Ephestiodes spp., Epiblema spp., Epiehoristodes spp., Epinotia spp.,Epiphyas spp., Epiplema spp., Epipsestis spp., Epirrhoe spp., Episimusspp., Epitymbia spp., Epilachna spp., Erannis spp., Erastria spp.,Eremnus spp., Ereunetis spp., Eriophyes spp., Eriosoma spp., Eriosomalanigerum, Erythroneura spp., Estigmene spp., Ethmia spp., Etiella spp.,Euagrotis spp., Eucosma spp., Euehlaena spp., Euelidia spp., Eueosmaspp., Euchistus spp., Eucosmomorpha spp., Eudonia spp., Eufidonia spp.,Euhyponomeutoides spp., Eulepitodes spp., Eulia spp., Eulithis spp.,Eupithecia spp., Euplexia spp., Eupoecilia spp., Eupoecilia ambiguella,Euproctis spp., Eupsilia spp., Eurhodope spp., Eurois spp., Eurygasterspp., Eurythmia spp., Eustrotia spp., Euxoa spp., Euzophera spp.,Evergestis spp., Evippe spp., Exartema spp., Fannia spp., Faronta spp.,Feltia spp., Filatima spp., Fishia spp., Frankliniella spp., Fumibotysspp., Gaesa spp., Gasgardia spp., Gastrophilus spp., Gelechia spp.,Gilpinia spp., Gilpinia polytoma, Glossina spp., Glyphipterix spp.,Glyphodes spp., Gnorimoschemini spp., Gonodonta spp., Gortyna spp.,Gracillaria spp., Graphania spp., Grapholita spp., Grapholitha spp.,Gravitarmata spp., Gretchena spp., Griselda spp., Gryllotalpa spp.,Gynaephora spp., Gypsonoma spp., Hada spp., Haematopinus spp.,Halisidota spp., Harpipteryx spp., Harrisina spp., Hedya spp.,Helicoverpa spp., Heliophobus spp., Heliothis spp., Hellula spp.,Helotropa spp., Hemaris spp., Hercinothrips spp., Herculia spp.,Hermonassa spp., Heterogenea spp., Holomelina spp., Homadaula spp.,Homoeosoma spp., Homoglaea spp., Homohadena spp., Homona spp.,Homonopsis spp., Hoplocampa spp., Hoplodrina spp., Hoshinoa spp.,Hxalomma spp., Hydraecia spp., Hydriomena spp., Hyles spp., Hyloicusspp., Hypagyrtis spp., Hypatima spp., Hyphantria spp., Hyphantria cunea,Hypocala spp., Hypocoena spp., Hypodema spp., Hyppobosca spp., Hypsipylaspp., Hyssia spp., Hysterosia spp., Idaea spp., Idia spp., Ipimorphaspp., Isia spp., Isochorista spp., Isophrictis spp., Isopolia spp.,Isotrias spp., Ixodes spp., Itame spp., Jodia spp., Jodis spp., Kawabeaspp., Keiferia spp., Keiferia lycopersicella, Labdia spp., Lacinipoliaspp., Lambdina spp., Lamprothritpa spp., Laodelphax spp., Lasius spp.,Laspeyresia spp., Leptinotarsa spp., Leptinotarsa decemlineata,Leptocorisa spp., Leptostales spp., Lecanium spp., Lecanium comi,Lepidosaphes spp., Lepisma spp., Lepisma saccharina, Lesmone spp.,Leucania spp., Leucinodes spp., Leucophaea spp., Leucophaea maderae,Leucoptera spp., Leucoptera scitella, Linognathus spp., Liposcelis spp.,Lissorhoptrus spp., Lithacodia spp., Lithocolletis spp., Lithomoia spp.,Lithophane spp., Lixodessa spp., Lobesia spp., Lobesia botrana,Lobophora spp., Locusta spp., Lomanaltes spp., Lomographa spp.,Loxagrotis spp., Loxostege spp., Lucilia spp., Lymantria spp., Lymnaeciaspp., Lyonetia spp., Lyriomyza spp., Macdonnoughia spp., Macrauzataspp., Macronoctua spp., Macrosiphus spp., Malacosoma spp., Maliarphaspp., Mamestra spp., Mamestra brassicae, Manduca spp., Manduca sexta,Marasmia spp., Margaritia spp., Matratinea spp., Matsumuraeses spp.,Melanagromyza spp., Melipotes spp., Melissopus spp., Melittia spp.,Melolontha spp., Meristis spp., Meritastis spp., Merophyas spp.,Mesapamea spp., Mesogona spp., Mesoleuca spp., Metanema spp.,Metendothenia spp., Metzneria spp., Micardia spp., Microcorses spp.,Microleon spp., Mnesictena spp., Mocis spp., Monima spp., Monochroaspp., Monomorium spp., Monomorium pharaonis, Monopsis spp., Morrisoniaspp., Musca spp., Mutuuraia spp., Myelois spp., Mythimna spp., Myzusspp., Naranga spp., Nedra spp., Nemapogon spp., Neodiprion spp.,Neosphaleroptera spp., Nephelodes spp., Nephotettix spp., Nezara spp.,Nilaparvata spp., Niphonympha spp., Nippoptilia spp., Noctua spp., Nolaspp., Notocelia spp., Notodonta spp., Nudaurelia spp., Ochropleura spp.,Ocnerostoma spp., Oestrus spp., Olethreutes spp., Oligia spp., Olindiaspp., Olygonychus spp., Olygonychus gallinae, Oncocnemis spp.,Operophtera spp., Ophisma spp., Opogona spp., Oraesia spp., Orniodorosspp., Orgyia spp., Oria spp., Orseolia spp., Orthodes spp., Orthogoniaspp., Orthosia spp., Oryzaephilus spp., Oscinella spp., Oscinella frit,Osminia spp., Ostrinia spp., Ostrinia nubilalis, Otiorhynchus spp.,Ourapteryx spp., Pachetra spp., Pachysphinx spp., Pagyda spp.,Paleacrita spp., Paliga spp., Palthis spp., Pammene spp., Pandemis spp.,Panemeria spp., Panolis spp., Panolis flammea, Panonychus spp.,Parargyresthia spp., Paradiarsia spp., Paralobesia spp., Paranthrenespp., Parapandemis spp., Parapediasia spp., Parastichtis spp.,Parasyndemis spp., Paratoria spp., Pareromeme spp., Pectinophora spp.,Pectinophora gossypiella, Pediculus spp., Pegomyia spp., Pegomyiahyoscyami, Pelochrista spp., Pennisetia spp., Penstemonia spp.,Pemphigus spp., Peribatodes spp., Peridroma spp., Perileucoptera spp.,Periplaneta spp., Perizoma spp., Petrova spp., Pexicopia spp., Phaloniaspp., Phalonidia spp., Phaneta spp., Phlyctaenia spp., Phlyctinus spp.,Phorbia spp., Phragmatobia spp., Phricanthes spp., Phthorimaea spp.,Phthorimaea operculella, Phyllocnistis spp., Phyllocoptruta spp.,Phyllocoptruta oleivora, Phyllonorycter spp., Phyllophila spp.,Phylloxera spp., Pieris spp., Pieris rapae, Piesma spp., Planococusspp., Planotortrix spp., Platyedra spp., Platynota spp., Platyptiliaspp., Platysenta spp., Plodia spp., Plusia spp., Plutella spp., Plutellaxylostella, Podosesia spp., Polia spp., Popilliaspp., Polymixis spp.,Polyphagotarsonemus spp., Polyphagotarsonemus latus, Prays spp.,Prionoxystus spp., Probole spp., Proceras spp., Prochoerodes spp.,Proeulia spp., Proschistis spp., Proselena spp., Proserpinus spp.,Protagrotis spp., Proteoteras spp., Protobathra spp., Protoschinia spp.,Pselnophorus spp., Pseudaletia spp., Pseudanthonomus spp.,Pseudaternelia spp., Pseudaulacaspis spp., Pseudexentera spp.,Pseudococus spp., Pseudohermenias spp., Pseudoplusia spp., Psoroptesspp., Psylla spp., Psylliodes spp., Pterophorus spp., Ptycholoma spp.,Pulvinaria spp., Pulvinaria aethiopica, Pyralis spp., Pyrausta spp.,Pyrgotis spp., Pyrreferra spp., Pyrrharctia spp., Quadraspidiotus spp.,Rancora spp., Raphia spp., Reticultermes spp., Retinia spp., Rhagoletisspp, Rhagoletis pomonella, Rhipicephalus spp., Rhizoglyphus spp.,Rhizopertha spp., Rhodnius spp., Rhophalosiphum spp., Rhopobota spp.,Rhyacia spp., Rhyacionia spp., Rhynchopacha spp., Rhyzosthenes spp.,Rivula spp., Rondotia spp., Rusidrina spp., Rynchaglaea spp., Sabulodesspp., Sahlbergella spp., Sahlbergella singularis, Saissetia spp., Samiaspp., Sannina spp., Sanninoidea spp., Saphoideus spp., Sarcoptes spp.,Sathrobrota spp., Scarabeidae, Sceliodes spp., Schinia spp.,Schistocerca spp., Schizaphis spp., Schizura spp., Schreckensteiniaspp., Sciara spp., Scirpophaga spp., Scirthrips auranti, Scoparia spp.,Scopula spp., Scotia spp., Scotinophara spp., Scotogramma spp.,Scrobipalpa spp., Scrobipalpopsis spp., Semiothisa spp., Sereda spp.,Sesamia spp., Sesia spp., Sicya spp., Sideridis spp., Simyra spp.,Sineugraphe spp., Sitochroa spp., Sitobion spp., Sitophilus spp.,Sitotroga spp., Solenopsis spp., Smerinthus spp., Sophronia spp.,Spaelotis spp., Spargaloma spp., Sparganothis spp., Spatalistis spp.,Sperchia spp., Sphecia spp., Sphinx spp., Spilonota spp., Spodopteraspp., Spodoptera littoralis, Stagmatophora spp., Staphylinochrous spp.,Stathmopoda spp., Stenodes spp., Sterrha spp., Stomoxys spp., Strophedraspp., Sunira spp., Sutyna spp., Swammerdamia spp., Syllomatia spp.,Sympistis spp., Synanthedon spp., Synaxis spp., Syncopacma spp.,Syndemis spp., Syngrapha spp., Synthomeida spp., Tabanus spp.,Taeniarchis spp., Taeniothrips spp., Tannia spp., Tarsonemus spp.,Tegulifera spp., Tehama spp., Teleiodes spp., Telorta spp., Tenebriospp., Tephrina spp., Teratoglaea spp., Terricula spp., Tethea spp.,Tetranychus spp., Thalpophila spp., Thaumetopoea spp., Thiodia spp.,Thrips spp., Thrips palmi, Thrips tabaci, Thyridopteryx spp., Thyrisspp., Tineola spp., Tipula spp., Tortricidia spp., Tortrix spp., Tracheaspp., Trialeurodes spp., Trialeurodes vaporariorum, Triatoma spp.,Triaxomera spp., Tribolium spp., Tricodectes spp., Trichoplusia spp.,Trichoplusia ni, Trichoptilus spp., Trioza spp., Trioza erytreae,Triphaenia spp., Triphosa spp., Trogoderma spp., Tyria spp., Udea spp.,Unaspis spp., Unaspis citri, Utetheisa spp., Valeriodes spp., Vespaspp., Vespamima spp., Vitacea spp., Vitula spp., Witlesia spp., Xanthiaspp., Xanthorhoe spp., Xanthotype spp., Xenomicta spp., Xenopsylla spp.,Xenopsylla cheopsis, Xestia spp., Xylena spp., Xylomyges spp., Xyrosarisspp., Yponomeuta spp., Ypsolopha spp., Zale spp., Zanclognathus spp.,Zeiraphera spp., Zenodoxus spp., Zeuzera spp., Zygaena spp.,

It is also possible to control pests of the class Nematoda using thecompounds according to the invention. Such pests include, for example,

root knot nematodes, cyst-forming nematodes and also stem and leafnematodes;

especially of Heterodera spp., e.g. Heterodera schachtii, Heterodoraavenae and Heterodora trifolii; Globodera spp., e.g. Globoderarostochiensis; Meloidogyne spp., e.g. Meloidogyne incognita andMeloidogyne javanica; Radopholus spp., e.g. Radopholus similis;Pratylenchus, e.g. Pratylenchus neglectans and Pratylenchus penetrans;Tylenchulus, e.g. Tylenchulus semipenetrans; Longidorus, Trichodorus,Xiphinema, Ditylenchus, Apheenchoides and Anguina; especiallyMeloidogyne, e.g. Meloidogyne incognita, and Heterodera, e.g. Heteroderaglycines.

An especially important aspect of the present invention is the use ofthe compounds of formula (I) according to the invention in theprotection of plants against parasitic feeding pests.

The action of the compounds according to the invention and thecompositions comprising them against animal pests can be significantlybroadened and adapted to the given circumstances by the addition ofother insecticides, acaricides or nematicides. Suitable additivesinclude, for example, representatives of the following classes of activeingredient: organophosphorus compounds, nitrophenols and derivatives,formamidines, ureas, carbamates, pyrethroids, chlorinated hydrocarbons,neonicotinoids and Bacillus thuringiensis preparations.

Examples of especially suitable mixing partners include: azamethiphos;chlorfenvinphos; cypermethrin, cypermethrin high-cis; cyromazine;diafenthiuron; diazinon; dichlorvos; dicrotophos; dicyclanil;fenoxycarb; fluazuron; furathiocarb; isazofos; iodfenphos; kinoprene;lufenuron; methacriphos; methidathion; monocrotophos; phosphamidon;profenofos; diofenolan; a compound obtainable from the Bacillusthuringiensis strain GC91 or from strain NCTC11821; pymetrozine;bromopropylate; methoprene; disulfoton; quinalphos; taufluvalinate;thiocyclam; thiometon; aldicarb; azinphos-methyl; benfuracarb;bifenthrin; buprofezin; carbofuran; dibutylaminothio; cartap;chlorfluazuron; chlorpyrifos; clothianidin; cyfluthrin;lambda-cyhalothrin; alpha-cypermethrin; zeta-cypermethrin; deltamethrin;diflubenzuron; endosulfan; ethiofencarb; fenitrothion; fenobucarb;fenvalerate; formothion; methiocarb; heptenophos; imidacloprid;isoprocarb; methamidophos; methomyl; mevinphos; parathion;parathion-methyl; phosalone; pirimicarb; propoxur; teflubenzuron;terbufos; triazamate; fenobucarb; tebufenozide; fipronil;beta-cyfluthrin; silafluofen; fenpyroximate; pyridaben; pyridalyl;fenazaquin; pyriproxyfen; pyrimidifen; nitenpyram; acetamiprid;emamectin; emamectin-benzoate; spinosad; a plant extract that is activeagainst insects; a preparation that comprises nematodes and is activeagainst insects; a preparation obtainable from Bacillus subtilis; apreparation that comprises fungi and is active against insects; apreparation that comprises viruses and is active against insects;chlorfenapyr; acephate; acrinathrin; alanycarb; alphamethrin; amitraz;AZ 60541; azinphos A; azinphos M; azocyclotin; bendiocarb; bensultap;beta-cyfluthrin; brofenprox; bromophos A; bufencarb; butocarboxin;butylpyridaben; cadusafos; carbaryl; carbophenothion; chloethocarb;chlorethoxyfos; chlormephos; cis-resmethrin; clocythrin; clofentezine;cyanophos; cycloprothrin; cyhexatin; demeton M; demeton S;demeton-S-methyl; dichlofenthion; dicliphos; diethion; dimethoate;dimethylvinphos; dioxathion; edifenphos; esfenvalerate; ethion;ethofenprox; ethoprophos; etrimphos; fenamiphos; fenbutatin oxide;fenothiocarb; fenpropathrin; fenpyrad; fenthion; fluazinam;flucycloxuron; flucythrinate; flufenoxuron; flufenprox; fonophos;fosthiazate; fubfenprox; HCH; hexaflumuron; hexythiazox; flonicamid;iprobenfos; isofenphos; isoxathion; ivermectin; malathion; mecarbam;mesulfenphos; metaldehyde; metolcarb; milbemectin; moxidectin; naled; NC184; nithiazine; omethoate; oxamyl; oxydemethon M; oxydeprofos;permethrin; phenthoate; phorate; phosmet; phoxim; pirimiphos M;pirimiphos E; promecarb; propaphos; prothiofos; prothoate; pyrachlophos;pyradaphenthion; pyresmethrin; pyrethrum; tebufenozide; salithion;sebufos; sulfotep; sulprofos; tebufenpyrad; tebupirimphos; tefluthrin;temephos; terbam; tetrachlorvinphos; thiacloprid; thiafenox;thiamethoxam; thiodicarb; thiofanox; thionazin; thuringiensin;tralomethrin; triarathene; triazophos; triazuron; trichlorfon;triflumuron; trimethacarb; vamidothion; xylylcarb; etoxazole;zetamethrin; indoxacarb; methoxyfenozide; bifenazate; XMC (3,5-xylylmethylcarbamate); or the fungus pathogen Metarhizium anisopliae.

The compounds according to the invention can be used to control, i.e. toinhibit or destroy, pests of the mentioned type occurring on plants,especially on useful plants and ornamentals in agriculture, inhorticulture and in forestry, or on parts of such plants, such as thefruits, blossoms, leaves, stems, tubers or roots, while in some casesplant parts that grow later are still protected against those pests.

Target crops include especially cereals, such as wheat, barley, rye,oats, rice, maize and sorghum; beet, such as sugar beet and fodder beet;fruit, e.g. pomes, stone fruit and soft fruit, such as apples, pears,plums, peaches, almonds, cherries and berries, e.g. strawberries,raspberries and blackberries; leguminous plants, such as beans, lentils,peas and soybeans; oil plants, such as rape, mustard, poppy, olives,sunflowers, coconut, castor oil, cocoa and groundnuts; cucurbitaceae,such as marrows, cucumbers and melons; fibre plants, such as cotton,flax, hemp and jute; citrus fruits, such as oranges, lemons, grapefruitand mandarins; vegetables, such as spinach, lettuce, asparagus,cabbages, carrots, onions, tomatoes, potatoes and paprika; lauraceae,such as avocado, cinnamon and camphor; and tobacco, nuts, coffee,aubergines, sugar cane, tea, pepper, vines, hops, bananas, naturalrubber plants and ornamentals.

Further areas of use of the compounds according to the invention are theprotection of stored goods and storerooms and the protection of rawmaterials, and also in the hygiene sector, especially the protection ofdomestic animals and productive livestock against pests of the mentionedtype, more especially the protection of domestic animals, especiallycats and dogs, from infestation by fleas, ticks and nematodes.

The invention therefore relates also to pesticidal compositions, such asemulsifiable concentrates, suspension concentrates, directly sprayableor dilutable solutions, spreadable pastes, dilute emulsions, wettablepowders, soluble powders, dispersible powders, wettable powders, dusts,granules and encapsulations of polymer substances, that comprise atleast one of the compounds according to the invention, the choice offormulation being made in accordance with the intended objectives andthe prevailing circumstances.

The active ingredient is used in those compositions in pure form, asolid active ingredient, for example, in a specific particle size, orpreferably together with at least one of the adjuvants customary informulation technology, such as extenders, e.g. solvents or solidcarriers, or surface-active compounds (surfactants). In the area ofparasite control in humans, domestic animals, productive livestock andpets it will be self-evident that only physiologically tolerableadditives are used.

Solvents are, for example: non-hydrogenated or partly hydrogenatedaromatic hydrocarbons, preferably fractions C₈ to C₁₂ of alkylbenzenes,such as xylene mixtures, alkylated naphthalenes ortetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such asparaffins or cyclohexane, alcohols, such as ethanol, propanol orbutanol, glycols and ethers and esters thereof, such as propyleneglycol, dipropylene glycol ether, ethylene glycol or ethylene glycolmonomethyl or -ethyl ether, ketones, such as cyclohexanone, isophoroneor diacetone alcohol, strongly polar solvents, such asN-methylpyrrolid-2-one, dimethyl sulfoxide or N,N-dimethylformamide,water, non-epoxidized or epoxidized plant oils, such as non-epoxidizedor epoxidized rapeseed, castor, coconut or soya oil, and silicone oils.

The solid carriers used, for example for dusts and dispersible powders,are as a rule natural rock powders, such as calcite, talc, kaolin,montmorillonite or attapulgite. Highly disperse silicic acids or highlydisperse absorbent polymers can also be added to improve the physicalproperties. Granular-adsorptive granule carriers are porous types, suchas pumice, crushed brick, sepiolite or bentonite, and non-sorbentcarrier materials are calcite or sand. A large number of granularmaterials of inorganic or organic nature can furthermore be used, inparticular dolomite or comminuted plant residues.

Surface-active compounds are, depending on the nature of the activecompound to be formulated, nonionic, cationic and/or anionic surfactantsor surfactant mixtures with good emulsifying, dispersing and wettingproperties. The surfactants listed below are to be regarded only asexamples; many other surfactants which are customary in formulationtechnology and are suitable according to the invention are described inthe relevant literature.

Nonionic surfactants are, in particular, polyglycol ether derivatives ofaliphatic or cycloaliphatic alcohols, saturated or unsaturated fattyacids and alkylphenols, which can contain 3 to 30 glycol ether groupsand 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to18 carbon atoms in the alkyl radical of the alkylphenols. Substanceswhich are furthermore suitable are water-soluble polyethylene oxideadducts, containing 20 to 250 ethylene glycol ether and 10 to 100propylene glycol ether groups, on propylene glycol, ethylenediaminopolypropylene glycol and alkyl polypropylene glycol having 1 to10 carbon atoms in the alkyl chain. The compounds mentioned usuallycontain 1 to 5 ethylene glycol units per propylene glycol unit. Examplesare nonylphenol-polyethoxyethanols, castor oil polyglycol ethers,polypropylene-polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol andoctylphenoxypolyethoxyethanol. Other substances are fatty acid esters ofpolyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.

The cationic surfactants are, in particular, quaternary ammonium saltswhich contain, as substituents, at least one alkyl radical having 8 to22 C atoms and, as further substituents, lower, non-halogenated orhalogenated alkyl, benzyl or lower hydroxyalkyl radicals. The salts arepreferably in the form of halides, methyl-sulfates or ethyl-sulfates.Examples are stearyl-trimethyl-ammonium chloride andbenzyl-di-(2-chloroethyl)-ethyl-ammonium bromide.

Suitable anionic surfactants can be both water-soluble soaps andwater-soluble synthetic surface-active compounds. Suitable soaps are thealkali metal, alkaline earth metal and substituted or unsubstitutedammonium salts of higher fatty acids (C₁₀-C₂₂), such as the sodium orpotassium salts of oleic or stearic acid, or of naturally occurringfatty acid mixtures, which can be obtained, for example, from coconutoil or tall oil; and furthermore also the fatty acid methyl-taurinesalts. However, synthetic surfactants are more frequently used, inparticular fatty sulfonates, fatty sulfates, sulfonated benzimidazolederivatives or alkylarylsulfonates. The fatty sulfonates and sulfatesare as a rule in the form of alkali metal, alkaline earth metal orsubstituted or unsubstituted ammonium salts and in general have an alkylradical of 8 to 22 C atoms, alkyl also including the alkyl moiety ofacyl radicals; examples are the sodium or calcium salt of ligninsulfonicacid, of dodecylsulfuric acid ester or of a fatty alcohol sulfatemixture prepared from naturally occurring fatty acids. These alsoinclude the salts of sulfuric acid esters and sulfonic acids of fattyalcohol-ethylene oxide adducts. The sulfonated benzimidazole derivativespreferably contain 2 sulfonic acid groups and a fatty acid radicalhaving about 8 to 22 C atoms. Alkylarylsulfonates are, for example, thesodium, calcium or triethanolammonium salts of dodecylbenzenesulfonicacid, of dibutylnaphthalenesulfonic acid or of a naphthalenesulfonicacid-formaldehyde condensation product. Corresponding phosphates, suchas salts of the phosphoric acid ester of a p-nonylphenol-(4-14)-ethyleneoxide adduct or phospholipids, can further also be used.

The compositions as a rule comprise 0.1 to 99%, in particular 0.1 to95%, of active compound and 1 to 99.9%, in particular 5 to 99.9%, of—atleast—one solid or liquid auxiliary, it being possible as a rule for 0to 25%, in particular 0.1 to 20%, of the composition to be surfactants(% is in each case percent by weight). While concentrated compositionsare more preferred as commercial goods, the end user as a rule usesdilute compositions which comprise considerably lower concentrations ofactive compound. Preferred compositions are composed, in particular, asfollows (%=percent by weight): Emulsifiable concentrates: activeingredient: 1 to 90%, preferably 5 to 20% surfactant: 1 to 30%,preferably 10 to 20% solvent: 5 to 98%, preferably 70 to 85% Dusts:active ingredient: 0.1 to 10%, preferably 0.1 to 1% solid carrier: 99.9to 90%, preferably 99.9 to 99% Suspension concentrates: activeingredient: 5 to 75%, preferably 10 to 50% water: 94 to 24%, preferably88 to 30% surfactant: 1 to 40%, preferably 2 to 30% Wettable powders:active ingredient: 0.5 to 90%, preferably 1 to 80% surfactant: 0.5 to20%, preferably 1 to 15% solid carrier: 5 to 99%, preferably 15 to 98%Granules: active ingredient: 0.5 to 30%, preferably 3 to 15% solidcarrier: 99.5 to 70%, preferably 97 to 85%

The compositions according to the invention may also comprise furthersolid or liquid adjuvants, such as stabilisers, e.g. vegetable oils orepoxidised vegetable oils (e.g. epoxidised coconut oil, rapeseed oil orsoybean oil), antifoams, e.g. silicone oil, preservatives, viscosityregulators, binders and/or tackifiers as well as fertilisers or otheractive ingredients for obtaining special effects, e.g. acaricides,bactericides, fungicides, nematicides, molluscicides or selectiveherbicides.

The crop protection products according to the invention are prepared inknown manner, in the absence of adjuvants, e.g. by grinding, sievingand/or compressing a solid active ingredient or mixture of activeingredients, for example to a certain particle size, and in the presenceof at least one adjuvant, for example by intimately mixing and/orgrinding the active ingredient or mixture of active ingredients with theadjuvant(s). The invention relates likewise to those processes for thepreparation of the compositions according to the invention and to theuse of the compounds of formula (I) in the preparation of thosecompositions.

The invention relates also to the methods of application of the cropprotection products, i.e. the methods of controlling pests of thementioned type, such as spraying, atomising, dusting, coating, dressing,scattering or pouring, which are selected in accordance with theintended objectives and the prevailing circumstances, and to the use ofthe compositions for controlling pests of the mentioned type. Typicalrates of concentration are from 0.1 to 1000 ppm, preferably from 0.1 to500 ppm, of active ingredient. The rates of application per hectare aregenerally from 1 to 2000 g of active ingredient per hectare, especiallyfrom 10 to 1000 g/ha, preferably from 20 to 600 g/ha, more especiallyfrom 20 to 100 g/ha.

A preferred method of application in the area of crop protection isapplication to the foliage of the plants (foliar application), thefrequency and the rate of application being dependent upon the risk ofinfestation by the pest in question. However, the active ingredient canalso penetrate the plants through the roots (systemic action) when thelocus of the plants is impregnated with a liquid formulation or when theactive ingredient is incorporated in solid form into the locus of theplants, for example into the soil, e.g. in granular form (soilapplication). In the case of paddy rice crops, such granules may beapplied in metered amounts to the flooded rice field.

The crop protection products according to the invention are alsosuitable for protecting plant propagation material, e.g. seed, such asfruits, tubers or grains, or plant cuttings, against animal pests. Thepropagation material can be treated with the composition beforeplanting: seed, for example, can be dressed before being sown. Theactive ingredients according to the invention can also be applied tograins (coating), either by impregnating the seeds in a liquidformulation or by coating them with a solid formulation. The compositioncan also be applied to the planting site when the propagation materialis being planted, for example to the seed furrow during sowing. Theinvention relates also to such methods of treating plant propagationmaterial and to the plant propagation material so treated.

The following Examples serve to illustrate the invention. They do notlimit the invention. Temperatures are given in degrees Celsius; mixingratios of solvents are given in parts by volume.

PREPARATION EXAMPLES Example A1.14′-desoxy-4′-(methoxycarbonyl-hydrazono)-avermectin B1 monosaccharide

2 g 4′-desoxy-4′-oxo-avermectin B1 monosaccharide are dissolved in 20 mlmethanol, 25 ml pyridine, 0.1 ml acetic acid and 0.4 ghydrazinecarboxylic acid methyl ester are added. The mixture is stirredat room tempertaure for 18 hours, then the solvent is removed in vacuo.The residue is extracted with dichloromethane and aqueous sodiumbicarbonate, the organic phase is dried over sodium sulfate and thesolvent is distilled off. The residue is purified by chromatography onsilica gel with hexane/ethyl acetate, yielding4′-desoxy-4′-(methoxycarbonyl-hydrazono)-avermectin B1 monosaccharide.

Example A2.1 4′-desoxy-4′-(phenylamino-carbonyl-hydrazono)-avermectin B1monosaccharide

Step 1: 10 g 4′-desoxy-4′-oxo-5-O-t-butyldimethylsilyl-avermectin B1monosaccharide are dissolved in 65 ml methanol, 100 ml pyridine, 1 mlacetic acid and 2 g N-phenyl-hydrazinecarboxamide are added. The mixtureis stirred at room tempertaure for 48 hours, then the solvent is removedin vacuo. The residue is extracted with dichloromethane and aqueoussodium bicarbonate, the organic phase is dried over sodium sulfate andthe solvent is distilled off. The residue is purified by chromatographyon silica gel with hexane/ethyl acetate, yielding4′-desoxy-4′-(phenylamino-carbonyl-hydrazono)-5-O-t-butyldimethylsilyl-avermectinB1 monosaccharide.

Step 2: 7 g4′-desoxy-4′-(phenylamino-carbonyl-hydrazono)-5-O-t-butyldimethylsilyl-avermectinB1 monosaccharide are dissolved in 75 ml tetrahydrofuran, then 25 ml ofa stock solution are added, which is prepared from 250 g 70% HF-Pyridin,275 ml tetrahydrofuran and 125 ml pyridine. The mixture is stirred atroom temperature for 24 hours, poured into water, and extracted withethyl acetate. Then the phases are separated; the organic phase is driedover sodium sulfate and the solvents are distilled off. The residue ispurified by chromatography on silica gel with hexane/ethyl acetate,yielding 4′-desoxy-4′-(phenylaminocarbonyl-hydrazono)-avermectin B1monosaccharide.

Example A3.1 4′-desoxy-4′-[(4-chloro-benzoyl)-hydrazono]-avermectin B1monosaccharide

3 g 4′-desoxy-4′-oxo-avermectin B1 monosaccharide are dissolved in 20 mlmethanol, 30 ml pyridine, 0.3 ml acetic acid and 0.7 g 4-chloro-benzoicacid hydrazide are added. The mixture is stirred at room tempertaure for48 hours, then the solvent is removed in vacuo. The residue is extractedwith dichloromethane and aqueous sodium bicarbonate, the organic phaseis dried over sodium sulfate and the solvent is distilled off. Theresidue is purified by chromatography on silica gel with hexane/ethylacetate, yielding 4′-desoxy-4′-[(4-chlorobenzoyl)-hydrazono]-avermectinB1 monosaccharide.

Example A3.12 4′-desoxy-4′-(tert-butyloxycarbonyloxy-imino)-avermectinB1 monosaccharide

300 mg 4′-desoxy-4′-hydroxyimino-5-O-t-butyldimethylsilyl-avermectin B1monosaccharide are dissolved in 3 ml dichloromethane, 86 mgdimethylaminopyridine, 142 μl pivalic anhydride are added. The mixtureis stirred at room temperature for 1 hour, the solvent is removed invacuo after filtration on silica gel with dichloromethane. The residueis used without additionnal purification. The residue is dissolved in7.5 ml tetrahydrofuran, then 1.5 ml of a stock solution are added, whichis prepared from 250 g 70% HF-Pyridin, 275 ml tetrahydrofuran and 125 mlpyridine. The mixture is stirred at room temperature for 24 hours,poured into water, and extracted with ethyl acetate. Then the phases areseparated; the organic phase is dried over sodium sulfate and thesolvents are distilled off. The residue is purified by chromatography onsilica gel with hexane/ethyl acetate, yielding4′-desoxy-4′-(tert-butylcarbonyloxy-imino)-avermectin B1 monosaccharide.

Example A4.1 4′-desoxy-4′-(methoxy-imino)-avermectin B1 monosaccharide

3 g 4′-desoxy-4′-oxo-avermectin B1 monosaccharide are dissolved in 20 mlmethanol, 30 ml pyridine and 2.2 g O-methyl-hydroxylamine hydrochlorideare added. The mixture is stirred at room tempertaure for 12 hours, thenthe solvent is removed in vacuo. The residue is purified bychromatography on silica gel with hexane/ethyl acetate, yielding4′-desoxy-4′-(methoxy-imino)-avermectin B1 monosaccharide.

Example A4.12 4′-desoxy-4′-(methoxymethyloxy-imino)-avermectin B1monosaccharide

10 g 4′-desoxy-4′-oxo-5-O-t-butyldimethylsilyl-avermectin B1monosaccharide are dissolved in 94 ml methanol, 2.03 ml pyridine and 1.8g O-Methoxymethyl-hydroxylamine are added. The mixture is stirred atroom temperature for 2 days, then the solvent is removed in vacuo. Theresidue is used without additionnal purification. A part of the residue(0.300 mg) is dissolved in 7.5 ml tetrahydrofuran, then 1.5 ml of astock solution are added, which is prepared from 250 g 70% HF-Pyridin,275 ml tetrahydrofuran and 125 ml pyridine. The mixture is stirred atroom temperature for 24 hours, poured into water, and extracted withethyl acetate. Then the phases are separated; the organic phase is driedover sodium sulfate and the solvents are distilled off. The residue ispurified by chromatography on silica gel with hexane/ethyl acetate,yielding: 4′-desoxy-4′-(methoxymethyloxy-imino)-avermectin B1monosaccharide.

Example A5.1 4″-desoxy-4″-(phenoxycarbonyl-hydrazono)-avermectin B1

4″-desoxy-4″-(phenoxycarbonyl-hydrazono)-avermectin B1 is obtained from4″-desoxy-4″-oxo-avermectin B1 and hydrazinecarboxylic acid phenyl esterby the same method as described for Example A1.1.

Example A5.4 4″-desoxy-4″-(methyloxycarbonyloxy-imino)-avermectin B1

300 mg 4″-desoxy-4″-hydroxyimino-5-O-t-butyldimethylsilyl-avermectin B1are dissolved in 3 ml dichloromethane, 73 mg dimethylaminopyridine, 46μl methyl chloroformate are added. The mixture is stirred at roomtemperature for 1 hour, then the solvent is removed in vacuo afterfiltration on silica gel with dichloromethane. The residue is usedwithout additionnal purification for the next step. The residue isdissolved in 7.5 ml tetrahydrofuran, then 1.5 ml of a stock solution areadded, which is prepared from 250 g 70% HF-Pyridin, 275 mltetrahydrofuran and 125 ml pyridine. The mixture is stirred at roomtemperature for 24 hours, poured into water, and extracted with ethylacetate. Then the phases are separated; the organic phase is dried oversodium sulfate and the solvents are distilled off. The residue ispurified by chromatography on silica gel with hexane/ethyl acetate,yielding 4″-desoxy-4″-(methyloxycarbonyloxy-imino)-avermectin B1.

Example A6.1 4″-desoxy-4″-(phenylamino-carbonyl-hydrazono)-avermectin B1

4″-desoxy-4″-(phenylamino-carbonyl-hydrazono)-avermectin B1 is obtainedfrom 4″-desoxy-4″-oxo-5-O-t-butyldimethylsilyl-avermectin B1 andN-phenyl-hydrazinecarboxamide by the same method as described forExample A2.1.

Example A7.1 4″-desoxy-4″-[(4-chloro-benzoyl)-hydrazono]-avermectin B1

4″-desoxy-4″-[(4-chloro-benzoyl)-hydrazono]-avermectin B1 is obtainedfrom 4″-desoxy-4″-oxo-avermectin B1 and 4-chloro-benzoic acid hydrazideby the same method as described for Example A3.1.

Example A7.23 4″-desoxy-4″-(acetatoxy-imino)-avermectin B1

300 mg 4″-desoxy-4″-hydroxyimino-5-O-t-butyldimethylsilyl-avermectin B1are dissolved in 3 ml dichloromethane, 40 mg dimethylaminopyridine, 32μl acetic anhydride are added. The mixture is stirred at roomtemperature for 1 hour, then 40 mg dimethylamino-pyridine, 32 μl aceticanhydride are added again. The solvent is removed in vacuo afterfiltration on silica gel with dichloromethane. The residue is usedwithout additionnal purify-cation. The residue is dissolved in 7.5 mltetrahydrofuran, then 1.5 ml of a stock solution are added, which isprepared from 250 g 70% HF-Pyridin, 275 ml tetrahydrofuran and 125 mlpyridine. The mixture is stirred at room temperature for 24 hours,poured into water, and extracted with ethyl acetate. Then the phases areseparated; the organic phase is dried over sodium sulfate and thesolvents are distilled off. The residue is purified by chromatography onsilica gel with hexane/ethyl acetate, yielding4″-desoxy-4″-(acetatoxy-imino)-avermectin B1.

Example A8.1 4″-desoxy-4″-(n-hexyloxy-imino)-avermectin B1

4″-desoxy-4″-(n-hexyloxy-imino)-avermectin B1 is obtained from4″-desoxy-4″-oxo-avermectin B1 and O-n-hexyl-hydroxylamine hydrochlorideby the same method as described for Example A4.1.

Similarly to the preparation examples above it is also possible toprepare the compounds listed in Tables A1 to A8 and Tables 1 to 216. Inthe Tables, the symbol

denotes—where necessary—the bond through which the radical in questionis attached to the N-, O- or C-atom of the skeleton.

Since in most cases the compounds are present as mixtures of theavermectin derivatives B1a and B1b, characterization by customaryphysical data such as melting point or refractive index makes littlesense. For this reason, the compounds are characterized by the retentiontimes which are determined in an analysis by HPLC (high performanceliquid chromatography). Here, the term B1a refers to the main componentin which R₁ is sec-butyl, with a content of usually more than 80%. B1bdenotes the minor component in which R₁ is isopropyl. Where tworetention times are given either for the B1a derivative, for the B1bderivative, or for both, the compounds are mixtures of E/Z isomers whichcan be separated chromatographically. In the case of compounds where aretention time is given only in column B1a or only in column B1b, thepure B1a or B1b component, respectively, can be obtained during work-up.The correct structures of the B1a and B1b components are assigned bymass spectrometry.

The following method is used for HPLC analysis: HPLC gradient conditionsSolvent A: 0.01% of trifluoroacetic acid in H₂O Solvent B: 0.01% oftrifluoroacetic acid in CH₃CN Time [min] A [%] B [%] Flow rate [μl/min]0 80 20 500 0.1 50 50 500 10 5 95 500 15 0 100 500 17 0 100 500 17.1 8020 500 22 80 20 500 Type of column YMC-Pack ODS-AQ Column length 125 mmInternal diameter of column: 2 mm Temperature 40° C.

The YMC-Pack ODS-AQ column used for the chromatography of the compoundsis manufactured by YMC, Alte Raesfelderstrasse 6, 46514 Schermbeck,Germany. TABLE A1 Compounds of the formula (I) wherein R₁ is sec-butylor isopropyl

Retention time (min) No. R₃ Z Q X-Y B1a B1b A1.1 methyl —C(═O)— NH—CH═CH— 8.51 7.84 A1.2 phenyl —C(═O)— NH —CH═CH— 9.93, 9.29 8.49

TABLE A2 Compounds of the formula (I) in which R₁ is sec-butyl orisopropyl.

Retention time (min) No. R₆ R₇ Z Q X-Y B1a B1b A2.1 Phenyl H —C(═O)— NH—CH═CH— 9.98, 9.34, 8.91 8.27

TABLE A3 Compounds of the formula (I) in which R₁ is sec-butyl orisopropyl

Retention time (min) No R₃ Z Q X-Y B1a B1b A3.1

—C(═O)— NH —CH═CH— 10.80  A3.2 methyl —C(═O)— NH —CH═CH— 7.59 A3.3

—C(═O)— NH —CH═CH— 7.02 A3.4 phenyl —C(═O)— NH —CH═CH— 8.46 A3.5

—C(═O)— NH —CH═CH— 9.99 A3.6

—C(═O)— NH —CH═CH— 6.19 A3.7 n-heptyl —C(═O)— NH —CH═CH— 11.65  A3.8

—C(═O)— NH —CH═CH— 9.18 8.48 A3.9

—C(═O)— NH —CH═CH— 11.69  11.05  A3.10 benzyl —C(═O)— NH —CH═CH— 9.568.97 A3.11

—C(═O)— NH —CH═CH— 10.58 9.98 A3.12 tert-Butyl —C(═O)— O —CH═CH—10.78, 10.95  10.04, 10.30 A3.13 n-undecyl —C(═O)— O —CH═CH— 15.31 A3.14 CH₃—CH═CH— —C(═O)— O —CH═CH—  9.65, 9.92 A3.15 ethyl —C(═O)— O—CH═CH—  9.44, 7.71

TABLE A4 Compounds of the formula (I) in which R₁ is sec-butyl orisopropyl

Retention time (min) No. R₄ Q X-Y B1a B1b A4.1 methyl O —CH═CH— 10.68A4.2 benzyl O —CH═CH— 12.07 A4.3

O —CH═CH— 11.58 A4.4

O —CH═CH— 12.49 A4.5 allyl O —CH═CH— 11.34 A4.6 tert-butyl O —CH═CH—12.84 A4.7

O —CH═CH— 13.96 A4.8

O —CH═CH—  8.19 7.98 A4.9 H O —CH═CH—  8.13 A4.10 ethyl O —CH═CH— 11.11A4.11

O —CH═CH—  11.05, 10.78 A4.12 CH₃—O—CH₂— O —CH═CH—   9.83, 10.04 A4.13CH_(3l —O—CH) ₂—CH₂—O—CH₂— O —CH═CH—   9.96,  9.18, 10.26 9.50

TABLE A5 Compounds of the formula (I) in which R₁ is sec-butyl orisopropyl

Retention time (min) No. R₃ Z Q X-Y B1a B1b A5.1 phenyl —C(═O)— NH—CH═CH— 10.77, 10.11 A5.2 methyl —C(═O)— NH —CH═CH— 9.33 A5.3 tert-butyl—C(═O)— NH —CH═CH— 10.83 A5.4 methyl —C(═O)— O —CH═CH— 10.24, 9.49,10.67 9.92

TABLE A6 Compounds of the formula (I) in which R₁ is sec-butyl orisopropyl

Retention time (min) No. R₆ R₇ Z Q X-Y B1a B1b A6.1 phenyl H —C(═O)— NH—CH═CH— 9.76 9.12 11.28 A6.2 H H —C(═S)— N—CH₃ —CH═CH— 5.55 5.44 A6.3 HH —C(═O)— NH —CH═CH— 8.59 7.84 7.68 A6.4 methyl H —C(═S)— NH —CH═CH—10.74 10.04 A6.5 phenyl H —C(═S)— NH —CH═CH— 12.28 11.73 A6.6 tert-butylH —C(═S)— NH —CH═CH— 12.32 12.11 A6.7 H H —C(═S)— NH —CH═CH— 9.71 9.49

TABLE A7 Compounds of the formula (I) in which R₁ is sec-butyl orisopropyl

Retention time (min No. R₃ Z Z X-Y B1a B1b A7.1

—C(═O)— NH —CH═CH— 10.96 A7.2

—C(═O)— NH —CH═CH—  8.41 A7.3 pyrid-4-yl —C(═O)— NH —CH═CH—  8.48  7.82A7.4 n-heptyl —C(═O)— NH —CH═CH— 13.12 12.59 A7.5

—C(═O)— NH —CH═CH— 10.41 A7.6

—C(═O)— NH —CH═CH—  9.51 A7.7 phenyl —C(═O)— NH —CH═CH— 10.09 A7.8methyl —C(═O)— NH —CH═CH—  9.61 A7.9

—C(═O)— NH —CH═CH— 10.57 A7.10

—C(═O)— NH —CH═CH— 11.11 A7.11

—C(═O)— NH —CH═CH— 10.45 A7.12

—C(═O)— NH —CH═CH—  9.60 A7.13

—C(═O)— NH —CH═CH— 10.72 A7.14

—C(═O)— NH —CH═CH— 10.68 A7.15

—C(═O)— NH —CH═CH— 12.21 A7.16 N≡C—CH₂— —C(═O)— NH —CH═CH—  9.33 A7.17

—C(═O)— NH —CH═CH— 10.72 A7.18 benzyl —C(═O)— NH —CH═CH— 10.88 A7.192-naphthyl —C(═O)— NH —CH═CH— 11.09 A7.20

—C(═O)— NH —CH═CH— 10.61 A7.21 methyl —SO₂— NH —CH═CH—  9.01  8.32  8.16A7.22

—SO₂— NH —CH═CH— 10.88  9.55 10.24 A7.23 methyl —C(═O)— O —CH═CH— 10.45, 10.19 10.94 A7.24 n-undecyl —C(═O)— O —CH═CH—  16.39, 18.02A7.25 tert-Butyl —C(═O)— O —CH═CH—  11.73, 12.72 A7.26 CH₃—CH═CH——C(═O)— O —CH═CH—  11.20,  10.45, 11.88 11.20 A7.27 ethyl —C(═O)— O—CH═CH—  10.99,  10.29, 11.65 10.99 A7.28 H —C(═0)— O —CH═CH— 11.41

TABLE A8 Compounds of the formula (I) in which R₁ is sec-butyl orisopropyl

Retention time (min) No. R₄ Q X-Y B1a B1b A8.1 n-hexyl O —CH═CH— 16.1815.38 A8.2

O —CH═CH— 12.87 A8.3 allyl O —CH═CH— 12.31 11.98 A8.4 ethyl O —CH═CH—12.29 12.00 A8.5 benzyl O —CH═CH— 12.38 11.79 12.11 A8.6 tert-butyl O—CH═CH— 13.23 12.64 12.86 A8.7 Methyl O —CH═CH— 11.77 11.36 A8.8 H O—CH═CH— 9.29 8.84 A8.9 H O —CH₂—CH₂— 10.22 10.03

TABLE B Compounds of the formula (I) in which R₂ is R₃—Z—, R₃—O—Z— orR₄— No. R₃ or R₄ Q B.1 Methyl O B.2 Ethyl O B.3 —CH₂—C≡N O B.4 Allyl OB.5 n-propyl O B.6 iso-propyl O B.7

O B.8 benzyl O B.9 n-butyl O B.10 tert-butyl O B.11 s-butyl O B.12iso-butyl O B.13

O B.14

O B.15

O B.16

O B.17

O B.18

O B.19

O B.20

O B.21

O B.22

O B.23

O B.24

O B.25

O B.26

O B.27

O B.28

O B.29

O B.30

O B.31

O B.32

O B.33

O B.34

O B.35

O B.36

O B.37

O B.38

O B.39

O B.40

O B.41

O B.42

O B.43

O B.44

O B.45

O B.46

O B.47

O B.48

O B.49

O B.50

O B.51

O B.52

O B.53

O B.54

O B.55

O B.56

O B.57

O B.58 H NH B.59 CH₃—C(═O)— NH B.60 H₂N—C(═O)— NH B.61 HO—CH₂—CH₂— NHB.62 N≡C—CH₂—CH₂— NH B.63 methyl NH B.64 ethyl NH B.65 —CH₂—C≡N NH B.66allyl NH B.67 n-propyl NH B.68 iso-propyl NH B.69

NH B.70 benzyl NH B.71 n-butyl NH B.72 tert-butyl NH B.73 s-butyl NHB.74 iso-butyl NH B.75

NH B.76

NH B.77

NH B.78

NH B.79

NH B.80

NH B.81

NH B.82

NH B.83

NH B.84

NH B.85

NH B.86

NH B.87

NH B.88

NH B.89

NH B.90

NH B.91

NH B.92

NH B.93

NH B.94

NH B.95

NH B.96

NH B.97

NH B.98

NH B.99

NH B.100

NH B.101

NH B.102

NH B.103

NH B.104

NH B.105

NH B.106

NH B.107

NH B.108

NH B.109

NH B.110

NH B.111

NH B.112

NH B.113

NH B.114

NH B.115

NH B.116

NH B.117

NH B.118

NH B.119

NH B.120 H N—CH₃ B.121 CH₃—O(═O)— N—CH₃ B.122 H₂N—C(═O)— N—CH₃ B.123HO—CH₂—CH₂— N—CH₃ B.124 N≡C—CH₂—CH₂— N—CH₃ B.125 methyl N—CH₃ B.126ethyl N—CH₃ B.127 —CH₂—C≡N N—CH₃ B.128 allyl N—CH₃ B.129 n-propyl N—CH₃B.130 iso-propyl N—CH₃ B.131

N—CH₃ B.132 benzyl N—CH₃ B.133 n-butyl N—CH₃ B.134 tert-butyl N—CH₃B.135 s-butyl N—CH₃ B.136 iso-butyl N—CH₃ B.137

N—CH₃ B.138

N—CH₃ B.139

N—CH₃ B.140

N—CH₃ B.141

N—CH₃ B.142

N—CH₃ B.143

N—CH₃ B.144

N—CH₃ B.145

N—CH₃ B.146

N—CH₃ B.147

N—CH₃ B.148

N—CH₃ B.149

N—CH₃ B.150

N—CH₃ B.151

N—CH₃ B.152

N—CH₃ B.153

N—CH₃ B.154

N—CH₃ B.155

N—CH₃ B.156

N—CH₃ B.157

N—CH₃ B.158

N—CH₃ B.159

N—CH₃ B.160

N—CH₃ B.161

N—CH₃ B.162

N—CH₃ B.163

N—CH₃ B.164

N—CH₃ B.165

N—CH₃ B.166

N—CH₃ B.167

N—CH₃ B.168

N—CH₃ B.169

N—CH₃ B.170

N—CH₃ B.171

N—CH₃ B.172

N—CH₃ B.173

N—CH₃ B.174

N—CH₃ B.175

N—CH₃ B.176

N—CH₃ B.177

N—CH₃ B.178

N—CH₃ B.179

N—CH₃ B.180

N—CH₃

TABLE C Compounds of the formula (I) in which R₂ is —Z—N(R₆)R₇ No. R₆ R₇Q C.1 methyl H O C.2 ethyl H O C.3 —CH₂—C≡N H O C.4 allyl H O C.5n-propyl H O C.6 iso-propyl H O C.7

H O C.8 benzyl H O C.9 n-butyl H O C.10 tert-butyl H O C.11 s-butyl H OC.12 iso-butyl H O C.13

H O C.14

H O C.15

H O C.16

H O C.17

H O C.18

H O C.19

H O C.20

H O C.21

H O C.22

H O C.23

H O C.24

H O C.25

H O C.26

H O C.27

H O C.28

H O C.29

H O C.30

H O C.31

H O C.32

H O C.33

H O C.34

H O C.35

H O C.36

H O C.37

H O C.38

H O C.39

H O C.40

H O C.41

H O C.42

H O C.43

H O C.44

H O C.45

H O C.46

H O C.47

H O C.48

H O C.49

H O C.50

H O C.51

H O C.52

H O C.53

H O C.54

H O C.55

H O C.56

H O C.57

H O C.58 H H NH C.59 CH₃—C(=O)— H NH C.60 H₂N—O(=O)— H NH C.61HO—CH₂—CH₂— H NH C.62 N≡C—CH₂—CH₂— H NH C.63 methyl H NH C.64 ethyl H NHC.65 —CH₂—C≡N H NH C.66 allyl H NH C.67 n-propyl H NH C.68 iso-propyl HNH C.69

H NH C.70 benzyl H NH C.71 n-butyl H NH C.72 tert-butyl H NH C.73s-butyl H NH C.74 iso-butyl H NH C.75

H NH C.76

H NH C.77

H NH C.78

H NH C.79

H NH C.80

H NH C.81

H NH C.82

H NH C.83

H NH C.84

H NH C.85

H NH C.86

H NH C.87

H NH C.88

H NH C.89

H NH C.90

H NH C.91

H NH C.92

H NH C.93

H NH C.94

H NH C.95

H NH C.96

H NH C.97

H NH C.98

H NH C.99

H NH C.100

H NH C.101

H NH C.102

H NH C.103

H NH C.104

H NH C.105

H NH C.106

H NH C.107

H NH C.108

H NH C.109

H NH C.110

H NH C.111

H NH C.112

H NH C.113

H NH C.114

H NH C.115

H NH C.116

H NH C.117

H NH C.118

H NH C.119

H NH C.120 H H N—CH₃ C.121 CH₃—C(=O)— H N—CH₃ C.122 H₂N—C(=O)— H N—CH₃C.123 HO—CH₂—CH₂— H N—CH₃ C.124 N≡C—CH₂—CH₂— H N—CH₃ C.125 methyl HN—CH₃ C.126 ethyl H N—CH₃ C.127 —CH₂—C≡N H N—CH₃ C.128 allyl H N—CH₃C.129 n-propyl H N—CH₃ C.130 iso-propyl H N—CH₃ C.131

H N—CH₃ C.132 benzyl H N—CH₃ C.133 n-butyl H N—CH₃ C.134 tert-butyl HN—CH₃ C.135 s-butyl H N—CH₃ C.136 iso-butyl H N—CH₃ C.137

H N—CH₃ C.138

H N—CH₃ C.139

H N—CH₃ C.140

H N—CH₃ C.141

H N—CH₃ C.142

H N—CH₃ C.143

H N—CH₃ C.144

H N—CH₃ C.145

H N—CH₃ C.146

H N—CH₃ C.147

H N—CH₃ C.148

H N—CH₃ C.149

H N—CH₃ C.150

H N—CH₃ C.151

H N—CH₃ C.152

H N—CH₃ C.153

H N—CH₃ C.154

H N—CH₃ C.155

H N—CH₃ C.156

H N—CH₃ C.157

H N—CH₃ C.158

H N—CH₃ C.159

H N—CH₃ C.160

H N—CH₃ C.161

H N—CH₃ C.162

H N—CH₃ C.163

H N—CH₃ C.164

H N—CH₃ C.165

H N—CH₃ C.166

H N—CH₃ C.167

H N—CH₃ C.168

H N—CH₃ C.169

H N—CH₃ C.170

H N—CH₃ C.171

H N—CH₃ C.172

H N—CH₃ C.173

H N—CH₃ C.174

H N—CH₃ C.175

H N—CH₃ C.176

H N—CH₃ C.177

H N—CH₃ C.178

H N—CH₃ C.179

H N—CH₃ C.180

H N—CH₃ C.181 methyl methyl O C.182 ethyl methyl O C.183 —H₂—C≡N methylO C.184 allyl methyl O C.185 n-propyl methyl O C.186 iso-propyl methyl OC.187

methyl O C.188 benzyl methyl O C.189 n-butyl methyl O C.190 tert-butylmethyl O C.191 s-butyl methyl O C.192 iso-butyl methyl O C.193

methyl O C.194

methyl O C.195

methyl O C.196

methyl O C.197

methyl O C.198

methyl O C.199

methyl O C.200

methyl O C.201

methyl O C.202

methyl O C.203

methyl O C.204

methyl O C.205

methyl O C.206

methyl O C.207

methyl O C.208

methyl O C.209

methyl O C.210

methyl O C.211

methyl O C.212

methyl O C.213

methyl O C.214

methyl O C.215

methyl O C.216

methyl O C.217

methyl O C.218

methyl O C.219

methyl O C.220

methyl O C.221

methyl O C.222

methyl O C.223

methyl O C.224

methyl O C.225

methyl O C.226

methyl O C.227

methyl O C.228

methyl O C.229

methyl O C.230

methyl O C.231

methyl O C.232

methyl O C.233

methyl O C.234

methyl O C.235

methyl O C.236

methyl O C.237

methyl O C.238 H methyl NH C.239 CH₃—C(=O)— methyl NH C.240 H₂N—C(=O)—methyl NH C.241 HO—CH₂—CH₂— methyl NH C.242 N≡C—CH₂—CH₂— methyl NH C.243methyl methyl NH C.244 ethyl methyl NH C.245 —CH₂—C≡N methyl NH C.246allyl methyl NH C.247 n-propyl methyl NH C.248 iso-propyl methyl NHC.249

methyl NH C.250 benzyl methyl NH C.251 n-butyl methyl NH C.252tert-butyl methyl NH C.253 s-butyl methyl NH C.254 iso-butyl methyl NHC.255

methyl NH C.256

methyl NH C.257

methyl NH C.258

methyl NH C.259

methyl NH C.260

methyl NH C.261

methyl NH C.262

methyl NH C.263

methyl NH C.264

methyl NH C.265

methyl NH C.266

methyl NH C.267

methyl NH C.268

methyl NH C.269

methyl NH C.270

methyl NH C.271

methyl NH C.272

methyl NH C.273

methyl NH C.274

methyl NH C.275

methyl NH C.276

methyl NH C.277

methyl NH C.278

methyl NH C.279

methyl NH C.280

methyl NH C.281

methyl NH C.282

methyl NH C.283

methyl NH C.284

methyl NH C.285

methyl NH C.286

methyl NH C.287

methyl NH C.288

methyl NH C.289

methyl NH C.290

methyl NH C.291

methyl NH C.292

methyl NH C.293

methyl NH C.294

methyl NH C.295

methyl NH C.296

methyl NH C.297

methyl NH C.298

methyl NH C.299

methyl NH C.300 H methyl N—CH₃ C.301 CH₃—O(=O)— methyl N—CH₃ C.302H₂N—C(=O)— methyl N—CH₃ C.303 HO—CH₂—CH₂— methyl N—CH₃ C.304N≡C—CH₂—CH₂— methyl N—CH₃ C.305 methyl methyl N—CH₃ C.306 ethyl methylN—CH₃ C.307 —CH₂—C≡N methyl N—CH₃ C.308 allyl methyl N—CH₃ C.309n-propyl methyl N—CH₃ C.310 iso-propyl methyl N—CH₃ C.311

methyl N—CH₃ C.312 benzyl methyl N—CH₃ C.313 n-butyl methyl N—CH₃ C.314tert-butyl methyl N—CH₃ C.315 s-butyl methyl N—CH₃ C.316 iso-butylmethyl N—CH₃ C.317

methyl N—CH₃ C.318

methyl N—CH₃ C.319

methyl N—CH₃ C.320

methyl N—CH₃ C.321

methyl N—CH₃ C.322

methyl N—CH₃ C.323

methyl N—CH₃ C.324

methyl N—CH₃ C.325

methyl N—CH₃ C.326

methyl N—CH₃ C.327

methyl N—CH₃ C.328

methyl N—CH₃ C.329

methyl N—CH₃ C.330

methyl N—CH₃ C.331

methyl N—CH₃ C.332

methyl N—CH₃ C.333

methyl N—CH₃ C.334

methyl N—CH₃ C.335

methyl N—CH₃ C.336

methyl N—CH₃ C.337

methyl N—CH₃ C.338

methyl N—CH₃ C.339

methyl N—CH₃ C.340

methyl N—CH₃ C.341

methyl N—CH₃ C.342

methyl N—CH₃ C.343

methyl N—CH₃ C.344

methyl N—CH₃ C.345

methyl N—CH₃ C.346

methyl N—CH₃ C.347

methyl N—CH₃ C.348

methyl N—CH₃ C.349

methyl N—CH₃ C.350

methyl N—CH₃ C.351

methyl N—CH₃ C.352

methyl N—CH₃ C.353

methyl N—CH₃ C.354

methyl N—CH₃ C.355

methyl N—CH₃ C.356

methyl N—CH₃ C.357

methyl N—CH₃ C.358

methyl N—CH₃ C.359

methyl N—CH₃ C.360

methyl N—CH₃ C.361 —CH₂—CH₂—CH₂—CH₂— O C.362 —CH₂—CH₂—CH₂—CH₂—CH₂— OC.363 —CH₂—CH₂—CH₂—CH₂—CH₂—CH₂— O C.364 —CH₂—CH₂—O—CH₂—CH₂— O C.365—CH₂—CH₂—S—CH₂—CH₂— O C.366 —CH₂—CH₂—SO₂—CH₂—CH₂— O C.367—CH₂—CH₂—S(=O)—CH₂—CH₂— O C.368 —CH₂—CH₂—NH—CH₂—CH₂— O C.369—CH₂—CH₂—N(CH₃)—CH₂—CH₂— O C.370 —CH₂—CH₂—N[—O(=O)—CH₃]—CH₂—CH₂— O C.371—CH₂—CH₂—CH₂—CH₂— NH C.372 —CH₂—CH₂—CH₂—CH₂—CH₂— NH C.373—CH₂—CH₂—CH₂—CH₂—CH₂—CH₂— NH C.374 —CH₂—CH₂—O—CH₂—CH₂— NH C.375—CH₂—CH₂—S—CH₂—CH₂— NH C.376 —CH₂—CH₂—SO₂—CH₂—CH₂— NH C.377—CH₂—CH₂—S(=O)—CH₂—CH₂— NH C.378 —CH₂—CH₂—NH—CH₂—CH₂— NH C.379—CH₂—CH₂—N(CH₃)—CH₂—CH₂— NH C.380 —CH₂—CH₂—N[—C(=O)—CH₃]—CH₂—CH₂— NHC.381 —CH₂—CH₂—CH₂—CH₂— N—CH₃ C.382 —CH₂—CH₂—CH₂—CH₂—CH₂— N—CH₃ C.383—CH₂—CH₂—CH₂—CH₂—CH₂—CH₂— N—CH₃ C.384 —CH₂—CH₂—O—CH₂—CH₂— N—CH₃ C.385—CH₂—CH₂—S—CH₂—CH₂— N—CH₃ C.386 —CH₂—CH₂—SO₂—CH₂—CH₂— N—CH₃ C.387—CH₂—CH₂—S(=O)—CH₂—CH₂— N—CH₃ C.388 —CH₂—CH₂—NH—CH₂—CH₂— N—CH₃ C.389—CH₂—CH₂—N(CH₃)—CH₂—CH₂— N—CH₃ C.390 —CH₂—CH₂—N[—C(=O)—CH₃]—CH₂—CH₂—N—CH₃

TABLE D Compounds of the formula (I) in which Q is NR₅ and R₂ is R₄ No.R₄ R₅ Q D.1 —CH₂—CH₂—CH₂—CH₂— N—R₅ D.2 —CH₂—CH₂—CH₂—CH₂—CH₂— N—R₅ D.3—CH₂—CH₂—CH₂—CH₂—CH₂—CH₂— N—R₅ D.4 —CH₂—CH₂—O—CH₂—CH₂— N—R₅ D.5—CH₂—CH₂—S—CH₂—CH₂— N—R₅ D.6 —CH₂—CH₂—SO₂—CH₂—CH₂— N—R₅ D.7—CH₂—CH₂—S(═O)—CH₂—CH₂— N—R₅ D.8 —CH₂—CH₂—NH—CH₂—CH₂— N—R₅ D.9—CH₂—CH₂—N(CH₃)—CH₂—CH₂— N—R₅ D.10 —CH₂—CH₂—N[—C(═O)—CH₃]—CH₂—CH₂— N—R₅

Table 1: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH═CH—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 2: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH═CH—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 3: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH₂CH₂—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 4: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH₂CH₂—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 5: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH═CH—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 6: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH═CH—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 7: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 8: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 9: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH═CH—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 10: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH═CH—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.1180 of Table B.

Table 11: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 12: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 13: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH═CH—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 14: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH═CH—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 15: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH₂CH₂—, Z is —C(═O)—, R₁ is cyclohexyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 16: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH₂CH₂—, Z is —C(═O)—, R₁ is cyclohexyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 17: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH═CH—, Z is —C(—S)—, R₁ is cyclohexyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 18: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH═CH—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 19: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is cyclohexyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 20: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is cyclohexyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 21: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH═CH—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 22: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH═CH—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 23: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 24: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 25: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH═CH—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 26: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH═CH—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 27: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH₂CH₂—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 28: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH₂CH₂—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 29: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH═CH—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 30: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH═CH—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 31: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 32: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 33: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH═CH—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 34: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH═CH—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 35: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 0,X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 36: Compounds of the formula (I) in which R₂ is R₃—O-Z-, n is 1,X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 37: Compounds of the formula (I) in which R₂ is (R₆)(R₇)N-Z-, n is0, X—Y is —CH═CH—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 38: Compounds of the formula (I) in which R₂ is (R₆)(R₇)N-Z-, n is1, X—Y is —CH═CH—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 39: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH₂CH₂—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 40: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH₂CH₂—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 41: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH═CH—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 42: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH═CH—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 43: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 44: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 45: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH═CH—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 46: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH═CH—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₅, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 47: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 48: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 49: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH═CH—, Z is —C(═O)—, R₁ is cyclohexyl and the combination ofR₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 50: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH═CH—, Z is —C(═O)—, R₁ is cyclohexyl and the combination ofR₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 51: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH₂CH₂—,Z is —C(═O)—, R₁ is cyclohexyl and the combination ofR₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 52: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH₂CH₂—,Z is —C(═O)—, R₁ is cyclohexyl and the combination ofR₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 53: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH═CH—, Z is —C(═S)—, R₁ is cyclohexyl and the combination ofR₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 54: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH═CH—, Z is —C(═S)—, R₁ is cyclohexyl and the combination ofR₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 55: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is cyclohexyl and the combinationof R₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 56: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is cyclohexyl and the combinationof R₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 57: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH═CH—, Z is —SO₂—, R₁ is cyclohexyl and the combination ofR₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 58: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH═CH—, Z is —SO₂—, R₁ is cyclohexyl and the combination ofR₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 59: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is cyclohexyl and the combination ofR₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 60: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is cyclohexyl and the combination ofR₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 61: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH═CH—, Z is —C(═O)—, R₁ is 1-methyl-butyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 62: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH═CH—, Z is —C(═O)—, R₁ is 1-methyl-butyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 63: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH₂CH₂—, Z is —C(═O)—, R₁ is 1-methyl-butyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 64: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH₂CH₂—, Z is —C(═O)—, R₁ is 1-methyl-butyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 65: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH═CH—, Z is —C(═S)—, R₁ is 1-methyl-butyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 66: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH═CH—, Z is —C(═S)—, R₁ is 1-methyl-butyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 67: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is 1-methyl-butyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 68: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is 1-methyl-butyl and thecombination of R₆, R₇ and Q for each compound corresponds to a line C.1to C.390 of Table C.

Table 69: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH═CH—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combinationof R₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 70: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH═CH—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combinationof R₆, R₇ and Q for each compound corresponds to a line 0.1 to C.390 ofTable C.

Table 71: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is0, X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combinationof R₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 72: Compounds of the formula (I) in which R₂ is -Z-N(R₆)(R₇), n is1, X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combinationof R₆, R₇ and Q for each compound corresponds to a line C.1 to C.390 ofTable C.

Table 73: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 74: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 75: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 76: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 77: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 78: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 79: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 80: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 81: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH═CH—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 82: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH═CH—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 83: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 84: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₃ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 85: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₃ andQ for each compound corresponds to a line B.1 to B.180 of Table B.

Table 86: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₃ andQ for each compound corresponds to a line B.1 to B.180 of Table B.

Table 87: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 88: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 89: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₃ andQ for each compound corresponds to a line B.1 to B.180 of Table B.

Table 90: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₃ andQ for each compound corresponds to a line B.1 to B.180 of Table B.

Table 91: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 92: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 93: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH═CH—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₃ and Qfor each compound corresponds to a line B.1 to B.180 of Table B.

Table 94: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH═CH—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₃ and Qfor each compound corresponds to a line B.1 to B.180 of Table B.

Table 95: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₃ andQ for each compound corresponds to a line B.1 to B.180 of Table B.

Table 96: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₃ andQ for each compound corresponds to a line B.1 to B.180 of Table B.

Table 97: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 98: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combination of R₃and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 99: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 100: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1,X—Y is —CH₂CH₂—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 101: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0,X—Y is —CH═CH—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 102: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1,X—Y is —CH═CH—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 103: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0,X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 104: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1,X—Y is —CH₂CH₂—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combinationof R₃ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 105: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0,X—Y is —CH═CH—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 106: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1,X—Y is —CH═CH—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 107: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 0,X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 108: Compounds of the formula (I) in which R₂ is R₃-Z-, n is 1,X—Y is —CH₂CH₂—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination ofR₃ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 109: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 110: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 111: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 112: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 113: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 114: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 115: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 116: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 117: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and the combinationof R₄ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 118: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and the combinationof R₄ and Q for each compound corresponds to a line B.1 to B.180 ofTable B.

Table 119: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 120: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line B.1 toB.180 of Table B.

Table 121: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₄ andQ for each compound corresponds to a line B.1 to B.180 of Table B.

Table 122: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₄ andQ for each compound corresponds to a line B.1 to B.180 of Table B.

Table 123: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₄and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 124: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₄and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 125: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₄ andQ for each compound corresponds to a line B.1 to B.180 of Table B.

Table 126: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₄ andQ for each compound corresponds to a line B.1 to B.180 of Table B.

Table 127: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₄and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 128: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₄and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 129: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₄ and Qfor each compound corresponds to a line B.1 to B.180 of Table B.

Table 130: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₄ and Qfor each compound corresponds to a line B.1 to B.180 of Table B.

Table 131: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₄ andQ for each compound corresponds to a line B.1 to B.180 of Table B.

Table 132: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₄ andQ for each compound corresponds to a line B.1 to B.180 of Table B.

Table 133: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 134: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 135: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combination ofR₄ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 136: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combination ofR₄ and a for each compound corresponds to a line B.1 to B.180 of TableB.

Table 137: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 138: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 139: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combination ofR₄ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 140: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combination ofR₄ and Q for each compound corresponds to a line B.1 to B.180 of TableB.

Table 141: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 142: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 143: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 144: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line B.1 to B.180 of Table B.

Table 145: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line D.1 toD.10 of Table D.

Table 146: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line D.1 toD.10 of Table D.

Table 147: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line D.1 toD.10 of Table D.

Table 148: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line D.1 toD.10 of Table D.

Table 149: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line D.1 toD.10 of Table D.

Table 150: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line D.1 toD.10 of Table D.

Table 151: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line D.1 toD.10 of Table D.

Table 152: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line D.1 toD.10 of Table D.

Table 153: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and the combinationof R₄ and Q for each compound corresponds to a line D.1 to D.10 of TableD.

Table 154: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and the combinationof R₄ and Q for each compound corresponds to a line D.1 to D.10 of TableD.

Table 155: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line D.1 toD.10 of Table D.

Table 156: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is sec-butyl or isopropyl and thecombination of R₄ and Q for each compound corresponds to a line D.1 toD.10 of Table D.

Table 157: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₄ andQ for each compound corresponds to a line D.1 to D.10 of Table D.

Table 158: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₄ andQ for each compound corresponds to a line D.1 to D.10 of Table D.

Table 159: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₄and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 160: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is cyclohexyl and the combination of R₄and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 161: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₄ andQ for each compound corresponds to a line D.1 to D.10 of Table D.

Table 162: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₄ andQ for each compound corresponds to a line D.1 to D.10 of Table D.

Table 163: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₄and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 164: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is cyclohexyl and the combination of R₄and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 165: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₄ and Qfor each compound corresponds to a line D.1 to D.10 of Table D.

Table 166: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₄ and Qfor each compound corresponds to a line D.1 to D.10 of Table D.

Table 167: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₄ andQ for each compound corresponds to a line D.1 to D.10 of Table D.

Table 168: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is cyclohexyl and the combination of R₄ andQ for each compound corresponds to a line D.1 to D.10 of Table D.

Table 169: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 170: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 171: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combination ofR₄ and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 172: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —C(═O)—, R₁ is 1-methyl-butyl and the combination ofR₄ and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 173: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 174: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 175: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combination ofR₄ and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 176: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —C(═S)—, R₁ is 1-methyl-butyl and the combination ofR₄ and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 177: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH═CH—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 178: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH═CH—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 179: Compounds of the formula (I) in which R₂ is R₄, n is 0, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Table 180: Compounds of the formula (I) in which R₂ is R₄, n is 1, X—Yis —CH₂CH₂—, Z is —SO₂—, R₁ is 1-methyl-butyl and the combination of R₄and Q for each compound corresponds to a line D.1 to D.10 of Table D.

Formulation examples for use in crop protection (%=percent by weight)EXAMPLE F1 Emulsion concentrates a) b) c) Active compound 25% 40% 50%Calcium dodecylbenzenesulphonate  5%  8%  6% Castor oil polyethyleneglycol ether  5% — — (36 mol of EO) Tributylphenol polyethylene glycolether — 12%  4% (30 mol of EO) Cyclohexanone — 15% 20% Xylene mixture65% 25% 20%

Mixing of finely ground active compound and additives gives an emulsionconcentrate which, by dilution with water, affords emulsions of thedesired concentration. EXAMPLE F2 Solutions a) b) c) d) activeingredient 80% 10%  5% 95% ethylene glycol monomethyl ether — 20% — —polyethylene glycol (MW 400) — 70% — — N-methylpyrrolid-2-one 20% — — —epoxidised coconut oil — —  1%  5% petroleum ether — — 94% — (boilingrange: 160-190°)

Mixing of finely ground active compound and additives gives a solutionsuitable for use in the form of microdrops. EXAMPLE F3 Granules a) b) c)d) Active compound 5% 10%  8% 21% Kaolin 94%  — 79% 54% Finely dividedsilicic acid 1% — 13%  7% Attapulgite — 90% — 18%

The active compound is dissolved in dichloromethane, the solution issprayed onto the mixture of carriers and the solvent is evaporated underreduced pressure. EXAMPLE F4 Wettable powder a) b) c) Active compound25% 50% 75% Sodium lignosulphonate  5%  5% — Sodium lauryl sulphate  3%—  5% Sodium diisobutylnaphthalene sulphonate —  6% 10% Octylphenolpolyethylene glycol ether —  2% — (7-8 mol of EO) Finely divided silicicacid  5% 10% 10% Kaolin 62% 27% —

Active compound and additives are mixed and the mixture is ground in asuitable mill. This gives wettable powders which can be diluted withwater to give suspensions of the desired concentration. EXAMPLE F5Emulsion concentrate Active compound 10% Octylphenol polyethylene glycolether (4-5 mol of EO)  3% Calcium dodecylbenzenesulphonate  3% Castoroil polyethylene glycol ether (36 mol of EO)  4% Cyclohexanone 30%Xylene mixture 50%

Mixing of finely ground active compound and additives gives an emulsionconcentrate which, by dilution with water, affords emulsions of thedesired concentration. EXAMPLE F6 Extruder granules Active compound 10%Sodium lignosulphonate  2% Carboxymethylcellulose  1% Kaolin 87%

Active compound and additives are mixed, the mixture is ground,moistened with water, extruded and granulated, and the granules aredried in a stream of air. EXAMPLE 7 Coated granules Active compound 3%Polyethylene glycol (MW 200) 3% Kaolin 94% 

In a mixer, the finely ground active compound is applied uniformly tothe kaolin which has been moistened with polyethylene glycol. This givesdust-free coated granules. EXAMPLE F8 Suspension concentrate Activecompound 40% Ethylene glycol 10% Nonylphenol polyethylene glycol ether(15 mol of EO)  6% Sodium lignosulphonate 10% Carboxymethylcellulose  1%Aqueous formaldehyde solution (37%) 0.2%  Aqueous silicone oil emulsion(75%) 0.8%  Water 32%Mixing of finely ground active compound and additives gives a suspensionconcentrate which, by dilution with water, affords suspensions of thedesired concentration.

BIOLOGICAL EXAMPLES Example B1 Activity Against Spodoptera Littoralis

Young soya bean plants are sprayed with an aqueous emulsion spray liquorwhich comprises 12.5 ppm of active compound, and, after the spraycoating has dried on, populated with 10 caterpillars of the first stageof Spodoptera littoralis and introduced into a plastic container. 3 dayslater, the reduction in the population in percent and the reduction inthe feeding damage in percent (% activity) are determined by comparingthe number of dead caterpillars and the feeding damage between thetreated and the untreated plants.

In this test, the compounds of the Tables A1 to A8 and Tables 1 to 216show good activity. Thus, in particular the compounds A1.1 to A8.9 aremore than 80% effective.

Example B2 Activity Against Spodoptera Littoralis, Systemic

Maize seedlings are placed into the test solution which comprises 12.5ppm of active compound. After 6 days, the leaves are cut off, placedonto moist filter paper in a Petri dish and populated with 12 to 15Spodoptera littoralis larvae of the L₁ stage. 4 days later, thereduction of the population in percent (% activity) is determined bycomparing the number of dead caterpillars between the treated and theuntreated plants.

In this test, the compounds of the Tables A1 to A8 and Tables 1 to 216show good activity. Thus, in particular the compounds A1.1 to A8.9 aremore than 80% effective.

Example B3 Activity Against Heliothis Virescens

30-35 0- to 24-hour-old eggs of Heliothis virescens are placed ontofilter paper in a Petri dish on a layer of synthetic feed. 0.8 ml of thetest solution which comprises 12.5 ppm of active compound is thenpipetted onto the filter papers. Evaluation is carried out after 6 days.The reduction in the population in percent (% activity) is determined bycomparing the number of dead eggs and larvae on the treated and theuntreated filter papers.

In this test, the compounds of the Tables A1 to A8 and Tables 1 to 216show good activity. Thus, in particular the compounds A1.1 to A8.9 aremore than 80% effective.

Example B4 Activity Against Plutella Xylostella Caterpillars

Young cabbage plants are sprayed with an aqueous emulsion spray liquorwhich comprises 12.5 ppm of the active compound. After the spray coatinghas dried on, the cabbage plants are populated with 10 caterpillars ofthe first stage of Plutella xylostella and introduced into a plasticcontainer. Evaluation is carried out after 3 days. The reduction in thepopulation in percent and the reduction in the feeding damage in percent(% activity) are determined by comparing the number of dead caterpillarsand the feeding damage on the treated and the untreated plants.

In this test, the compounds of the Tables A1 to A8 and Tables 1 to 216show good activity. Thus, in particular the compounds A1.1 to A8.9 aremore than 80% effective.

Example B5 Activity Against Frankliniella Occidentalis

In Petri dishes, discs of the leaves of beans are placed onto agar andsprayed with test solution which comprises 12.5 ppm of active compoundin a spraying chamber. The leaves are then populated with a mixedpopulation of Frankliniella occidentalis. Evaluation is carried outafter 10 days. The reduction in percent (% activity) is determined bycomparing the population on the treated leaves with that of theuntreated leaves.

In this test, the compounds of the Tables A1 to A8 and Tables 1 to 216show good activity. Thus, in particular the compounds A1.1 to A8.9 aremore than 80% effective.

Example B6 Activity Against Diabrotica Balteata

Maize seedlings are sprayed with an aqueous emulsion spray liquor whichcomprises 12.5 ppm of active compound and, after the spray coating hasdried on, populated with 10 larvae of the second stage of Diabroticabalteata and then introduced into a plastic container. After 6 days, thereduction in the population in percent (% activity) is determined bycomparing the dead larvae between the treated and the untreated plants.

In this test, the compounds of the Tables A1 to A8 and Tables 1 to 216show good activity. Thus, in particular the compounds A1.1 to A8.9 aremore than 80% effective.

Example B7 Activity Against Tetranychus Urticae

Young bean plants are populated with a mixed population of Tetranychusurticae and, after 1 day, sprayed with an aqueous emulsion spray liquorwhich comprises 12.5 ppm of active compound, incubated at 25° C. for 6days and then evaluated. The reduction in the population in percent (%activity) is determined by comparing the number of dead eggs, larvae andadults on the treated and on the untreated plants.

In this test, the compounds of the Tables A1 to A8 and Tables 1 to 216show good activity. Thus, in particular the compounds A1.1 to A8.9 aremore than 80% effective.

1. A compound of the formula

in which n is 0 or 1; X—Y is —CH═CH— or —CH₂—CH₂—; R₁ is C₁-C₁₂alkyl,C₃-C₈cycloalkyl or C₂-C₁₂alkenyl; and R₂ is R₃-Z-, R₃—O-Z-, R₄ or-Z-N(R₆)(R₇); Z is —C(═O)—, —C(═S)— or —SO₂—; Q is 0 or —N—R₅; R₃ and R₄are H, C₁-C₁₂alkyl, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl, C₃-C₁₂cycloalkyl,C₅-C₁₂cycloalkenyl, aryl or heterocyclyl, wherein the alkyl, alkenyl,alkynyl, cycloalkyl, cycloalkenyl, aryl and heterocyclyl radicals maybe—depending on the substitution possibilities—unsubstituted or mono- topentasubstituted; either R₅ is H, C₁-C₈alkyl, hydroxy-C₁-C₈alkyl,C₃-C₈cycloalkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, phenyl, benzyl, —C(═O)—R₉,or —CH₂—C(═O)—R₉; or, when Q is NR₅ and R₂ is R₄, R₄ and R₅ together area three- to seven-membered alkylene- or alkenylene-bridge, which isunsubstituted or mono- to tri-substituted; or a three- to seven-memberedalkylene- or alkenylene-bridge, which are unsubstituted or mono- totri-substituted, and in which one or two of the methylene groups of thebridge are replaced by O, NR₈, S, S(═O) or SO₂; R₆ and R₇ are,independently from each other, H, unsubstituted or mono- topentasubstituted C₁-C₁₂alkyl, unsubstituted or mono- to pentasubstitutedC₂-C₁₂alkenyl, unsubstituted or mono- to pentasubstituted C₂-C₁₂alkynyl,unsubstituted or mono- to pentasubstituted C₃-C₁₂-cycloalkyl,unsubstituted or mono- to pentasubstituted C₅-C₁₂cycloalkenyl,unsubstituted or mono- to pentasubstituted aryl, or unsubstituted ormono- to pentasubstituted heterocyclyl; or R₆ and R₇ together are athree- to seven-membered alkylene- or alkenylene-bridge, which areunsubstituted or mono- to tri-substituted; or a three- to seven-memberedalkylene- or alkenylene-bridge, which are unsubstituted or mono- totri-substituted, and in which one or two of the methylene groups of thebridge are replaced by O, NR₈, S, S(═O) or SO₂; R₈ is H, C₁-C₈alkyl,hydroxy-C₁-C₈alkyl, C₃-C₈cycloalkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, phenyl,benzyl, —C(═O)R₉ or —CH₂—C(═O)—R₉; in which the substituents of thealkyl, alkenyl, alkynyl, alkylene, alkenylene, cycloalkyl, cycloalkenyl,aryl and heterocyclyl radicals mentioned under R₂, R₃, R₄, R₅, R₆, R₇and R₈ are selected from the group consisting of OH, ═O, SH, ═S, —N₃,halogen, halo-C₁-C₂alkyl, CN, SCN, NO₂, trialkylsilyl, C₁-C₁₂alkyl,C₁-C₁₂-haloalkyl, C₂-C₈alkenyl, C₂-C₆haloalkenyl, C₂-C₈alkynyl,C₃-C₈cycloalkyl that is unsubstituted or substituted by one to threemethyl groups, norbornylenyl, C₃-C₈halocycloalkyl, C₁-C₁₂alkoxy,C₁-C₁₂alkoxy-C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₃-C₈cycloalkoxy,C₁-C₁₂alkylthio, C₃-C₈cycloalkylthio, C₁-C₁₂-haloalkylthio,C₁-C₁₂alkyl-sulfinyl, C₃-C₈cycloalkylsulfinyl, C₁-C₁₂haloalkylsulfinyl,C₃-C₈halocycloalkylsulfinyl, C₁-C₁₂alkylsulfonyl,C₃-C₈cycloalkylsulfonyl, C₁-C₁₂haloalkylsulfonyl,C₃-C₈halocycloalkylsulfonyl, —N(R₁₂)₂ wherein the two R₁₂ areindependent of each other, —C(═O)R₉, —O—C(═O)R₁₀, —NHC(═O)R₉,—S—C(═S)R₁₀, —P(═O)(OC₁-C₆alkyl)₂, —S(═O)₂R₁₃, —NH—S(═O)₂R₁₃,—OC(═O)—C₁-C₆alkyl-S(═O)₂R₁₃, aryl, benzyl, heterocyclyl, aryloxy,benzyloxy, heterocyclyloxy, arylthio, benzylthio and heterocyclylthio;wherein the aryl, heterocyclyl, aryloxy, benzyloxy, heterocyclyloxy,arylthio, benzylthio or heterocyclylthio radicals are unsubstituted or,depending on the possibilities of substitution on the ring, mono- topentasubstituted by substituents selected from the group consisting ofOH, halogen, CN, NO₂, C₁-C₁₂alkyl, C₃-C₈cycloalkyl, C₁-C₁₂haloalkyl,C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio,C₁-C₆alkoxy-C₁-C₆alkyl, dimethylamino-C₁-C₆alkoxy, C₂-C₈alkenyl,C₂-C₈alkynyl, phenyl, phenoxy, phenyl-C₁-C₆alkyl, methylene-dioxy,—C(═O)R₉, —O—C(═O)—R₁₀, —NH—C(═O)R₁₀, —N(R₁₂)₂ wherein the two R₁₂ areindependent of each other, C₁-C₆alkylsulfinyl, C₃-C₈cycloalkylsulfinyl,C₁-C₆haloalkylsulfinyl, C₃-C₈halo-cycloalkylsulfinyl,C₁-C₆alkylsulfonyl, C₃-C₈cycloalkylsulfonyl, C₁-C₆haloalkylsulfonyl andC₃-C₈halocycloalkylsulfonyl; R₉ is H, OH, SH, —N(R₁₂)₂ wherein the twoR₁₂ are independent of each other, C₁-C₂₄alkyl, C₂-C₁₂alkenyl,C₁-C₈hydroxyalkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy,C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkoxy,C₁-C₆alkoxy-C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₁₂alkylthio, C₂-C₈alkenyloxy,C₃-C₈alkynyloxy, —NH—C₁-C₆alkyl-C(═O)—R₁₁,—N(C₁-C₆alkyl)-C₁-C₆alkyl-C(═O)—R₁₁, —O—C₁-C₂alkyl-C(═O)R₁₁,—C₁-C₆alkyl-S(═O)₂R₁₃, aryl, benzyl, heterocyclyl, aryloxy, benzyloxy,heterocyclyloxy; or aryl, benzyl, heterocyclyl, aryloxy, benzyloxy orheterocyclyloxy, which are unsubstituted or mono- to trisubstituted inthe ring independently of one another by halogen, nitro, C₁-C₆alkyl,C₁-C₆alkoxy, C₁-C₆haloalkyl or C₁-C₆haloalkoxy; R₁₀ is H, C₁-C₂₄alkyl,C₁-C₁₂haloalkyl, C₁-C₁₂hydroxyalkyl, C₂-C₈alkenyl, C₂-C₈alkynyl,C₁-C₆alkoxy-C₁-C₆alkyl, —N(R₁₂)₂ wherein the two R₁₂ are independent ofeach other, —C₁-C₆alkyl-C(═O)R₁₂, —C₁-C₆alkyl-S(═O)₂R₁₃, aryl, benzyl,heterocyclyl; or aryl, benzyl or heterocyclyl which, depending on thepossibilities of substitution on the ring, are mono- to trisubstitutedby substituents selected from the group consisting of OH, halogen, CN,NO₂, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy,C₁-C₁₂alkylthio and C₁-C₁₂haloalkylthio; R₁₁ is H, OH, C₁-C₂₄alkyl thatis optionally subsituted with OH, or —S(═O)₂—C₁-C₆alkyl, C₂-C₁₂alkenyl,C₂-C₁₂alkynyl, C₁-C₁₂alkoxy, C₁-C₆ alkoxy-C₁-C₆alkyl,C₁-C₆alkoxy-C₁-C₆alkoxy, C₂-C₈alkenyloxy, aryl, aryloxy, benzyloxy,heterocyclyl, heterocyclyloxy or —N(R₁₂)₂, wherein the two R₁₂ areindependent of each other; R₁₂H, C₁-C₆alkyl, which is optionallysubstituted with one to five substituents selected from the groupconsisting of OH, ═O, halogen, C₁-C₆alkoxy, hydroxy and cyano;C₁-C₈-cycloalkyl, aryl, benzyl, heteroaryl; or aryl, benzyl orheteroaryl, which, depending on the possibilities of substitution on thering, are mono- to trisubstituted by substituents selected from thegroup consisting of OH, halogen, CN, NO₂, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl,C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylthio and C₁-C₁₂haloalkylthio;or the two R₁₂ together are a three- to seven-membered alkylene- oralkenylene-bridge, which is unsubstituted or mono- to tri-substituted;or a three- to seven-membered alkylene- or alkenylene-bridge, which isunsubstituted or mono- to tri-substituted, and in which one of themethylene groups of the bridge is replaced by O, NR₈, S, S(═O) or SO₂;R₁₃ is H, C₁-C₆alkyl that is optionally substituted with one to fivesubstituents selected from the group consisting of hydroxy, halogen, ═O,C₁-C₆alkoxy, hydroxy and cyano; aryl, benzyl, heteroaryl; or aryl,benzyl or heteroaryl, which, depending on the possibilities ofsubstitution on the ring, are mono- to trisubstituted by substituentsselected from the group consisting of OH, ═O, halogen, CN, NO₂,C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy,C₁-C₁₂alkylthio and C₁-C₁₂haloalkylthio; or, if appropriate, an E/Zisomer, E/Z isomer mixture and/or tautomer thereof, in each case in freeform or in salt form.
 2. A pesticide composition which contains at leastone compound of the formula (I) as described in claim 1 as activecompound and at least one auxiliary.
 3. A method for controlling pestswherein a composition as described in claim 2 is applied to the pests ortheir habitat.
 4. A process for preparing a composition as described inclaim 2 which contains at least one auxiliary, wherein the activecompound is mixed intimately and/or ground with the auxiliary(s). 5.(canceled)
 6. (canceled)
 7. A method for protecting plant propagationmaterial, wherein the propagation material or the location where thepropagation material is planted is treated, comprising applying thecomposition described in claim 2.